Benzenemethanamine, 3-chloro- → t-Butyl 4-(5-(3-chlorobenzylamino)-2-nitrophenyl)piperazine-1-carboxylate

HRID 1910528노트

반응식

HRID 1910528 반응식
F[C:2]1[CH:3]=[CH:4][C:5]([N+:21]([O-:23])=[O:22])=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:7]=1.[Cl:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28][NH2:29].C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28][NH:29][C:2]1[CH:3]=[CH:4][C:5]([N+:21]([O-:23])=[O:22])=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:7]=1

참가 물질

5

반응물 3

HCID 77802Benzenemethanamine, 3-chloro-HCID 81531DiisopropylethylamineHCID 22272537tert-Butyl 4-(5-Fluoro-2-nitrophenyl)piperazine-1-carboxylate

생성물 1

HCID 58707310t-Butyl 4-(5-(3-chlorobenzylamino)-2-nitrophenyl)piperazine-1-carboxylate수율 48%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

t-Butyl 4-(5-fluoro-2-nitrophenyl)piperazine-1-carboxylate (431 mg, 1.3 mmol), 3-chlorobenzylamine (187 mg, 1.3 mmol), N,N-diisopropylethylamine (342 mg, 1.3 mmol) were stirred at 80° C. in dry acetonitrile (25 mL) for 72 h. The solvent was evaporated and the residue was dissolved in dichloromethane and washed with water. The dichloromethane was evaporated and the crude compound was purified by silica chromatography using 25% ethyl acetate in hexanes to afford the title compound (277 mg, 48% yield). 1H NMR (400 MHz, CD3OD): δ 7.96 (d, 1H), 7.37-7.26 (m, 4H), 6.29 (d, 1H), 6.18 (s, 1H), 4.42 (s, 2H), 3.55 (m, 4H), 2.92 (m, 4H), 1.47 (s, 9H); MS (ESI) m/z: Calculated for C22H27ClN4O4: 446.17; Observed: 469.2 (M++Na).

후처리

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water
  4. customThe dichloromethane was evaporated
  5. customthe crude compound was purified by silica chromatography

출처 및 근거

ORD 기록
ord-230103ab97064207a912fd21b7ff15b4
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604021B2

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