Sodium borohydride → 3-Methyl-4-(2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethyl)benzonitrile

HRID 1519580Notes

Reaction equation

HRID 1519580 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1/[CH:10]=[CH:11]/[N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)[CH2:14][CH2:13]1)[C:5]#[N:6].[BH4-].[Na+]>CO.C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=2)[CH2:14][CH2:13]1)[C:5]#[N:6]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 866944743-methyl-4-((E)-2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}vinyl)benzonitrile

Product 1

HCID 675134573-Methyl-4-(2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-methyl-4-((E)-2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}vinyl)benzonitrile (100 mg, 0.24 mmol) in 15 mL of methanol and 10 mL of DCM was added NaBH4 (508 mg, 2.4 mmol), then stirred at room temperature overnight. The crude product was purified via prepare TLC (methanol/DCM 1:10) to give 3-methyl-4-(2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethyl)benzonitrile. 1H-NMR (300 MHz, CDCl3) δ ppm 8.12 (d, J=8.6 Hz, 2H), 7.23˜7.40 (m, 5H), 3.01˜3.21 (m, 2H), 2.80˜2.92 (m, 4H), 2.50˜2.65 (m, 10H), 2.33 (s, 3H). MS m/z: 379 (M+1)+. (0.062 μM)

Workup

  1. customThe crude product was purified
  2. customvia prepare TLC (methanol/DCM 1:10)

Sources & evidence

ORD record
ord-cfa18c14e1514bc6be233f3b03da9dd2
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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