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

HRID 1519590
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HRID 1519590 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-98918b38b4f44c52817aa36508552e5b
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09073882B2

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