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

HRID 1519596
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HRID 1519596 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[CH2:11][CH:12]=O)[C:6]#[N:7].[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>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[CH2:11][CH2:12][N:28]1[CH2:29][CH2:30][N:25]([CH2:24][CH2:23][C:20]2[CH:19]=[CH:18][C:17]([N+:14]([O-:16])=[O:15])=[CH:22][CH:21]=2)[CH2:26][CH2:27]1)[C:6]#[N:7]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 5049666Sodium triacetoxyborohydrideHCID 149859651-[2-(4-Nitrophenyl)ethyl]piperazineHCID 772306873-Methoxy-4-(2-oxoethyl)benzonitrile

생성물 1

HCID 680717893-Methoxy-4-(2-{4-[2-(4-nitrophenyl)ethyl]piperazin-1-yl}ethyl)benzonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 3-methoxy-4-(2-oxoethyl)benzonitrile (91 mg, 0.56 mmol), 1-[2-(4-nitrophenyl)ethyl]piperazine (110 mg, 0.56 mmol) and NaBH(OAc)3 (393 mg, 1.87 mmol) in anhydrous DCM (15 mL) was stirred at ambient temperature overnight. The reaction was completed according to TLC. The reaction mixture was added 15 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 8.15 (d, J=8.5 Hz, 3H), 7.37 (d, J=8.5 Hz, 3H), 7.05 (s, 1H), 3.85 (s, 3H), 2.85˜2.96 (m, 5H), 2.49˜2.75 (m, 11H). MS m/z: 395 (M+1)+. (0.30 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-ff1070270ea8484f9b0023e9d6a3e5cd
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09073882B2

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