Ethyl 1-(4-nitrophenyl)piperidine-4-carboxylate → 1-(4-Amino-phenyl)-piperidine-4-carboxylic acid ethyl ester

HRID 1510266노트

반응식

HRID 1510266 반응식
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[H][H]>CO.[Pd]>[CH2:1]([O:3][C:4]([CH:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[CH2:10][CH2:11]1)=[O:5])[CH3:2]

참가 물질

5

반응물 2

HCID 2796870Ethyl 1-(4-nitrophenyl)piperidine-4-carboxylateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 27641811-(4-Amino-phenyl)-piperidine-4-carboxylic acid ethyl ester

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A solution of 1-fluoro-4-nitrobenzene (2.0 g, 1.50 mL, 14 mmol), piperidine-4-carboxylic acid ethyl ester (2.2 g, 2.15 mL, 14 mmol), and potassium carbonate (9.7 g, 70 mmol) in CH3CN (20 mL) was stirred at room temperature overnight. The resulting mixture was filtered and concentrated. The residue was purified by chromatography on silica gel (gradient elution with 5-50% ethyl acetate in hexanes) to produce 2.0 g of 1-(4-nitro-phenyl)-piperidine-4-carboxylic acid ethyl ester as a yellow solid. 1.0 g of the above 1-(4-nitro-phenyl)-piperidine-4-carboxylic acid ethyl ester was hydrogenated using 10% Pd/C (200 mg) in MeOH, under 50 psi pressure of hydrogen for 2 hours. The catalyst was filtered, and the residue was concentrated to produce 1-(4-amino-phenyl)-piperidine-4-carboxylic acid ethyl ester. This material was directly used in the next step without further purification.

후처리

  1. filtrationThe catalyst was filtered
  2. concentrationthe residue was concentrated

출처 및 근거

ORD 기록
ord-8081823117e74210b7a208158f57aa50
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08211914B2

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