Sodium triacetoxyborohydride → 3-methyl-4-((E)-2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}vinyl)benzonitrile

HRID 1519579Notes

Reaction equation

HRID 1519579 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH2:10][CH:11]=O)[C:5]#[N:6].[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:18][CH:17]=1)([O-:15])=[O:14].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO>[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1/[CH:10]=[CH:11]/[N:27]1[CH2:28][CH2:29][N:24]([CH2:23][CH2:22][C:19]2[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:21][CH:20]=2)[CH2:25][CH2:26]1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 149859651-[2-(4-Nitrophenyl)ethyl]piperazineHCID 772306903-Methyl-4-(2-oxoethyl)benzonitrile

Product 1

HCID 866944743-methyl-4-((E)-2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}vinyl)benzonitrileYield 53.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-methyl-4-(2-oxoethyl)benzonitrile (130 mg, 0.8 mmol), 1-[2-(4-nitrophenyl)ethyl]piperazine (188 mg, 0.8 mmol) and NaBH(OAc)3 in 25 mL of dry methanol were stirred at room temperature over night. The solid was filtered to get 160 mg of 3-methyl-4-((E)-2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}vinyl)benzonitrile. 1H-NMR (300 MHz, CDCl3) δ ppm 8.15 (d, J=8.6 Hz, 2H), 7.31˜7.40 (m, 5H), 6.72 (d, J=13.5 Hz, 1H), 5.35 (d, J=13.9 Hz, 1H), 3.20 (s, 4H), 2.95 (s, 2H), 2.57˜2.75 (m, 6H), 2.26 (s, 3H). MS m/z: 377 (M+1)+.

Workup

  1. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-33a05f19606a406d88fa9fbe19583e3f
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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