Ammonium formate → (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazine

HRID 1379190

반응식

HRID 1379190 반응식
C([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:29])[C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=2)[C@H:10]([CH2:30][C:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[NH:33][CH:32]=2)[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C>[F:24][C:21]([F:22])([F:23])[C:19]1[CH:20]=[C:15]([CH:16]=[C:17]([C:25]([F:26])([F:27])[F:28])[CH:18]=1)[C:14]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][C@H:10]1[CH2:30][C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1)=[O:29]

참가 물질

4

반응물 2

HCID 2723923Ammonium formateHCID 54406912(2R)-4-benzyl-1-[3,5-bis(trifluoro-methyl)benzoyl]-2-(1H-indol-3-yl-methyl)piperazine

생성물 1

HCID 10972505(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazine수율 61.5%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of (2R)-4-benzyl-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)piperazine (5.20 g), ammonium formate (1.50 g) and 10% Pd charcoal (0.52 g) in ethanol (50 ml) was refluxed for 7.5 hours under nitrogen atmosphere. The reaction mixture was cooled to room temperature and filtered through Celite pad. The filtrate was concentrated under reduced pressure and the residue was purified on a silica gel column eluting with a mixture of dichloromethane and methanol (20:1) to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)piperazine (2.67 g, 61.5%) as a syrup.

후처리

  1. temperaturewas refluxed for 7.5 hours under nitrogen atmosphere
  2. filtrationfiltered through Celite pad
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified on a silica gel column
  5. washeluting with a mixture of dichloromethane and methanol (20:1)

출처 및 근거

ORD 기록
ord-b46cd4ad789e425888714dc8b8a244c3
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05670505

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