Sodium triacetoxyborohydride → 2,6-Difluoro-4-(2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethyl)benzonitrile

HRID 1519590Notes

Reaction equation

HRID 1519590 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([CH2:10][CH:11]=O)[CH:7]=[C:6]([F:13])[C:3]=1[C:4]#[N:5].[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:19][CH:18]=1)([O-:16])=[O:15].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:9]=[C:8]([CH2:10][CH2:11][N:28]2[CH2:29][CH2:30][N:25]([CH2:24][CH2:23][C:20]3[CH:19]=[CH:18][C:17]([N+:14]([O-:16])=[O:15])=[CH:22][CH:21]=3)[CH2:26][CH2:27]2)[CH:7]=[C:6]([F:13])[C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 103299452,6-Difluoro-4-(2-oxoethyl)benzonitrileHCID 149859651-[2-(4-Nitrophenyl)ethyl]piperazine

Product 1

HCID 680716652,6-Difluoro-4-(2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2,6-difluoro-4-(2-oxoethyl)benzonitrile (185 mg, 1.0 mmol), 1-[2-(4-nitrophenyl)ethyl]piperazine (200 mg, 0.85 mmol) and NaBH(OAc)3 (720 mg, 3.4 mmol) in anhydrous DCM (10 mL) was stirred at ambient temperature overnight. The reaction was completed according to TLC. The reaction mixture was added 20 mL of DCM, washed with brine, separated the organic layer, dried over anhydrous sodium sulfate and concentrated. The residue was purified by preparative TLC to give the product. 1H-NMR (400 MHz, CDCl3) δ ppm 8.15˜8.17 (d, J=8.6 Hz, 2H), 7.37˜7.39 (d, J=8.6 Hz, 2H), 6.92˜6.94 (d, J=8.6 Hz, 2H), 2.50˜3.11 (m, 16H). MS m/z: 401 (M+1)+. (0.16 μM)

Workup

  1. washwashed with brine
  2. customseparated the organic layer
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by preparative TLC
  6. customto give the product

Sources & evidence

ORD record
ord-98918b38b4f44c52817aa36508552e5b
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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