N-bromobutanimide → tert-Butyl 4-(4-amino-3-bromophenyl)-piperidine-1-carboxylate

HRID 1043279

반응식

HRID 1043279 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:21]N1C(=O)CCC1=O>C(Cl)Cl.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([Br:21])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 21940085tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate

생성물 1

HCID 56834849tert-Butyl 4-(4-amino-3-bromophenyl)-piperidine-1-carboxylate수율 103.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-(4-amino-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (0.20 g, 0.71 mmol) (as prepared in the previous step) in DCM (3 mL) was added N-bromosuccinimide (NBS) (0.13 g, 0.71 mmol), and the reaction stirred at RT for 10 h. The reaction was diluted with EtOAc (10 mL) and washed with NaHCO3 (2×10 mL) and brine (10 mL). Concentration of the organic layer gave 0.26 g (100%) of the title compound as a yellow foam. Mass spectrum (ESI, m/z): Calcd. for C16H23BrN2O2, 355.1 (M+H). found 355.1.

후처리

  1. washwashed with NaHCO3 (2×10 mL) and brine (10 mL)

출처 및 근거

ORD 기록
ord-42e57c650d74494a89e5254c998597e7
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557847B2

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