VILAZODONE SPECTRAL DATA

VILAZODONE

Vilazodone hydrochloride.png

Vilazodone hydrochloride; 163521-08-2; Vilazodone HCl; Viibryd; UNII-U8HTX2GK8J; EMD-68843

NO SYNTHESIS IS THIS POST, ONLY SPECTRAL DATA DISCUSSED

SEE MORE SPECTROSCOPY DATA AT………..http://orgspectroscopyint.blogspot.in/2015/06/vilazodone.html

ENJOY THE INTERPRETATIONS

Vilazodone (United States trade name Viibryd veye-brid) is a serotonergic antidepressant developed by Clinical Data for the treatment of major depressive disorder. The chemical compound was originally developed by Merck KGaA (Germany).^[2] Vilazodone was approved by the FDA for use in the United States to treat major depressive disorder in 2011.^[3]^[4]^[5]

Medical uses

According to two eight-week, randomized, double-blind, placebo-controlled trials in adults, vilazodone elicits an antidepressant response after one week of treatment. After eight weeks, subjects assigned to vilazodone 40 mg daily dose (titrated over 2 weeks) experienced a significantly higher response rate than the group given placebo (44% vs 30%, P = .002). Remission rates for vilazodone were not significantly different versus placebo.^[6]

According to an article on the United States approval of vilazodone written by FDA staff, “it is unknown whether [vilazodone] has any advantages compared to other drugs in the antidepressant class.”^[7]

PAPER FROM OPRD

Scale-Up Synthesis of Antidepressant Drug Vilazodone

Bin Hu , Qiao Song , and Yungen Xu *

Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing, 210009, P. R. China

Org. Process Res. Dev., 2012, 16 (9), pp 1552–1557

DOI: 10.1021/op300171m

http://pubs.acs.org/doi/full/10.1021/op300171m

A scale-up synthesis of antidepressant drug vilazodone was accomplished in five steps. Friedel–Crafts acylation of 1-tosyl-1H-indole-5-carbonitrile with 4-chlorobutyryl chloride, selective deoxygenation in NaBH₄/CF₃COOH system coupled with ethyl 5-(piperazin-1-yl)-benzofuran-2-carboxylate hydrochloride, one-step deprotection and esterolysis, and the final ammonolysis led to the target molecule vilazodone in 52.4% overall yield and 99.7% purity. This convenient and economical procedure is remarkably applicable for scale-up production.

5-(4-(3-(5-Cyano-1H-indol-3-yl)butyl)piperazin-1-yl)benzofuran-2-carboxamide (1)

To a solution of 6 (3 kg, 11.3 mol) in anhydrous DMF (150 L) at 15 °C was added CDI (1.6 kg, 10.2 mol). ……………………………………………….DELETED……………………to furnish the crude product of vilazodone hydrochloride 1 as off-white solid. The product of vilazodone hydrochloride was then recrystallized from an ethanol–methanol solution (1:1; 10 L) to give the final pure product vilazodone hydrochloride as white needles (2.4 kg, 81%). HPLC analysis: 99.7%. Mp: 234–236 °C (became charred).

¹H NMR (500 MHz, DMSO-d₆):

δ = 11.49 (s, 1H),

11.81 (bs, 1H),

8.10 (s, 1H),

7.61 (brs, 1H),

7.53 (d, J = 8.2 Hz, 1H),

7.52 (d, J = 8.2 Hz, 1H),

7.45 (d, J = 0.65 Hz, 1H),

7.41 (dd, J = 8.4 Hz, J = 1.6 Hz, 1H),

7.40 (d, J = 2.6 Hz, 1H),

7.27 (d, J = 2.4 Hz, 1H),

7.21 (dd, J = 9.1 Hz, J = 2.4 Hz, 1H),

3.78–3.70 (m, 2H), 3.58–3.52 (m, 2H),

3.23–3.21 (m, 6H),

2.78 (t, J = 7.5 Hz, 2H),

1.85–1.78 (m, 2H),

1.61–1.75 (m, 2H).

MS (ESI, 70 eV): m/z = 442 [M + H]⁺.

IR (KBr): 3458,

3128,

2216, NITRILE

1674, AMIDE

1597, 1400, 934 cm^–1.

¹³C NMR (75 MHz, DMSO-d₆): 22.9, 23.6, 26.8, 46.9 (2C), 50.9 (2C), 55.4, 100.1, 108.5, 109.8, 112.2, 112.7, 115.3, 118.5, 121.0, 123.6, 124.1, 125.1, 126.9, 127.7, 138.0, 146.7, 149.5, 149.6, 160.0.

HRMS (ESI): m/z [M + H]⁺ calcd for C₂₆H₂₈N₅O₂, 442.2238; found, 442.2234.

……………

WILL BE UPDATED

http://globalresearchonline.net/journalcontents/v29-1/35.pdf

file:///C:/Users/anthonyc/Downloads/lsyc_a_944268_sm4503.pdf

http://gxdxsrsp.cqvip.com/bitstream/123456789/13653/1/%E6%96%B0%E5%9E%8B%E6%8A%97%E6%8A%91%E9%83%81%E8%8D%AF%E7%BB%B4%E6%8B%89%E4%BD%90%E9%85%AE%E4%B8%AD%E9%97%B4%E4%BD%93%E7%9A%84%E5%90%88%E6%88%90%E5%B7%A5%E8%89%BA%E7%A0%94%E7%A9%B6

http://tuprints.ulb.tu-darmstadt.de/621/1/DissertationThiloMohrhardt.pdf

1H NMR PREDICT

13 C NMR PREDICT

will post a clear picture soon

…………………………

SEE MORE SPECTROSCOPY DATA AT………..http://orgspectroscopyint.blogspot.in/2015/06/vilazodone.html

VIIBRYD Tablets for oral administration contain polymorph Form IV vilazodone hydrochloride (HCl), a selective serotonin reuptake inhibitor and a 5HT_1A receptor partial agonist.

Vilazodone HCl is 2-benzofurancarboxamide, 5-[4-[4-(5cyano-1H-indol-3-yl)butyl]-1-piperazinyl]-, hydrochloride (1:1). Its molecular weight is 477.99. The structural formula is:

VIIBRYD® (vilazodone HCl) Structural Formula Illustration

In addition to the active ingredient, VIIBRYD Tablets contain lactose monohydrate, microcrystalline cellulose, magnesium stearate, colloidal silicon dioxide, polyvinyl alcohol, titanium dioxide, polyethylene glycol, talc, FD&C Blue #1 (40 mg only), FD&C Yellow #6 (20 mg only) and FD&C Red #40 (10 mg only).