Ethyl 4-piperidinecarboxylate → 1-[3-(4-Chloro-benzoylamino)-benzyl]-piperidine-4-carboxylic acid ethyl ester

HRID 1486720노트

반응식

HRID 1486720 반응식
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=O)[CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[NH:19]1[CH2:29][CH2:28][CH:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:26]([O:25][C:23]([CH:22]1[CH2:28][CH2:29][N:19]([CH2:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([NH:8][C:6](=[O:7])[C:5]3[CH:17]=[CH:18][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:10]=2)[CH2:20][CH2:21]1)=[O:24])[CH3:27]

참가 물질

6

반응물 4

HCID 70770Ethyl 4-piperidinecarboxylateHCID 516892Sodium BicarbonateHCID 23750934-chloro-N-(3-formylphenyl)benzamideHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 867065481-[3-(4-Chloro-benzoylamino)-benzyl]-piperidine-4-carboxylic acid ethyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 4-chloro-N-(3-formyl-phenyl)-benzamide (2.1 g, 8.09 mmol), ethyl isonipecotate (1.53 g, 9.55 mmol) in DCM (45 mL) is treated with sodium triacetoxy borohydride (2.5 g, 11.2 mmol) in 5 portions over 20 min. and the reaction mixture is stirred for 18 h at RT. Aq. sat. NaHCO3 (20 mL) is added and the mixture is stirred for 30 min. The phases are separated and the aqueous phase is extracted twice with DCM (50 ml). The combined organic phases are dried over MgSO4 and evaporated. The title compound is obtained as a colorless solid (3.24 g, 98%); LC-MS A: tR=0.72 min; [M+H]+=401.01.

후처리

  1. stirringthe mixture is stirred for 30 min
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted twice with DCM (50 ml)
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. customevaporated

출처 및 근거

ORD 기록
ord-a6b022559d5d4fa896cf050db2c9f0fe
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428456B2

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