Potassium Hydroxide → 4-[3-(4-Chloro-phenoxy)-benzyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 1255774

반응식

HRID 1255774 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[CH:29]=[CH:28][C:18]([O:19][C:20]2[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=2)[CH:23]=O)=[CH:17][CH:16]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[K+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:23][C:22]2[CH:25]=[CH:26][CH:27]=[C:20]([O:19][C:18]3[CH:28]=[CH:29][C:15]([Cl:14])=[CH:16][CH:17]=3)[CH:21]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 14797Potassium HydroxideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 6160153-(4-Chlorophenoxy)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 674135414-[3-(4-Chloro-phenoxy)-benzyl]-piperazine-1-carboxylic acid tert-butyl ester수율 75%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of piperazine-1-carboxylic acid tert-butyl ester (19.6 g, 105 mmol) and 3-(4-chloro-phenoxy)-benzaldehyde (24.4 g, 105 mmol) in THF (90 mL) was treated with NaB(OAc)3H (33.4 g, 158 mmol). After 3 h, the resulting mixture was treated with 10% aq. KOH (500 mL). The aqueous phase was extracted with EtOAc (2×500 mL) then saturated aqueous NaCl (200 mL). The organic extracts were combined, dried (MgSO4) and purified (FCC) to give 4-[3-(4-chloro-phenoxy)-benzyl]-piperazine-1-carboxylic acid tert-butyl ester (29.6 g, 75%). MS (ESI+): calcd for C22H27ClN2O3 m/z 402.17. found 403.2 (M+H)+.

후처리

  1. extractionThe aqueous phase was extracted with EtOAc (2×500 mL)
  2. dry with materialdried (MgSO4)
  3. custompurified (FCC)

출처 및 근거

ORD 기록
ord-bc062b3c02614b9fa219df479bfe9aae
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461159B2

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