Cyclohexylamine → HCID 22285581, 화합물

HRID 1062442노트

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HRID 1062442 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH:10]=[C:11]([CH:13]=O)[N:12]=1.[CH:22]1([NH2:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH:10]=[C:11]([CH2:13][NH:28][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[N:12]=1

참가 물질

5

반응물 3

HCID 7965CyclohexylamineHCID 4311764Sodium borohydrideHCID 22285566HCID 22285566, 화합물

생성물 1

HCID 22285581HCID 22285581, 화합물수율 81.2%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
4 °C

실험 절차

To a solution of 2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxaldehyde (62 mg, 0.20 mmol) in methanol (7 mL) was added cyclohexylamine (58 μL, 0.5 mmol). The mixture was stirred overnight, and cooled to 4° C. NaBH4 (40 mg, 1.1 mmol) was added. The mixture was stirred at rt for 1 h, and concentrated. The residue was dissolved in CH2Cl2, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by preparative TLC (50% EtOAc in hexane) to give N-{[2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazol-4-yl]methyl}-N-cyclohexylamine (65 mg, 81% yield): LC-MS m/z (400.7 MH+), retention time 2.32 min (method 1).

후처리

  1. stirringThe mixture was stirred at rt for 1 h
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by preparative TLC (50% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-d51f3ec1063740a7ba6ef9f75acf37d9
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06960601B2

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