Cyclohexanol → 4-(4-Cyclohexyloxy-benzyl)-piperazine-1-carboxylic acid phenylamide

HRID 40591

반응식

HRID 40591 반응식
[C:1]1([NH:7][C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:24]1(O)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C(Cl)Cl>[C:1]1([NH:7][C:8]([N:10]2[CH2:11][CH2:12][N:13]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([O:23][CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)=[CH:21][CH:22]=3)[CH2:14][CH2:15]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 7966CyclohexanolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 578808774-(4-Hydroxy-benzyl)-piperazine-1-carboxylic acid phenylamide

생성물 1

HCID 115602654-(4-Cyclohexyloxy-benzyl)-piperazine-1-carboxylic acid phenylamide수율 28%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of 4-(4-hydroxy-benzyl)-piperazine-1-carboxylic acid phenylamide (311 mg) and cyclohexanol (150 mg) in DCM (4 mL) was added polymer-supported Ph3P (500 mg) followed by di-tert-butyl azodicarboxylate (345 mg). The reaction mixture was shaken overnight, and filtered. Chromatography of the filtrate gave the title compound as a white solid (110 mg). 1H NMR (400 MHz, CDCl3): 7.36-7.19 (m, 6H), 7.05-7.00 (m, 1H), 6.88-6.84 (m, 2H), 6.30 (s, 1H), 4.25-4.20 (m, 1H), 3.50-3.47 (m, 6H), 2.48-2.46 (m, 4H), 2.01-1.97 (m, 2H), 1.82-1.80 (m, 2H), 1.60-1.29 (m, 6H).

후처리

  1. filtrationfiltered

출처 및 근거

ORD 기록
ord-da542b1dd56f49ae9b0c0d75241f7941
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530476B2

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