Pyridine → 1-benzyl-N-(5-bromo-2-hydroxyphenyl)piperidine-4-carboxamide

HRID 710084노트

반응식

HRID 710084 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[OH:9].N1C=CC=CC=1.[CH2:16]([N:23]1[CH2:28][CH2:27][CH:26]([C:29](Cl)=[O:30])[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[CH2:16]([N:23]1[CH2:28][CH2:27][CH:26]([C:29]([NH:1][C:2]2[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=2[OH:9])=[O:30])[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 3518402-Amino-4-BromophenolHCID 189197671-Benzylpiperidine-4-carbonyl chloride

생성물 1

HCID 711141861-benzyl-N-(5-bromo-2-hydroxyphenyl)piperidine-4-carboxamide수율 101.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

1-Benzylpiperidine-4-carboxylic acid (29 g, 0.13 mol) dissolved in DCM (300 ml), cooled to 0° C. and added oxalyl chloride (17.3 ml, 0.2 mol). Catalytic amount of DMF was added to this mixture and stirred at rt for 2 h. After 2 h, DCM removed on rotavapour and co-distilled the residue two times with DCM to obtain 1-benzylpiperidine-4-carbonyl chloride quantitatively. 2-Amino-4-bromophenol (23 g, 0.12 mol) dissolved in DCM and added pyridine (11.5 g, 0.15 mol) under nitrogen atmosphere. This mixture stirred at rt for 30 mins and added 1-benzylpiperidine-4-carbonyl chloride (29 g, 0.12 mol) in DCM (100 ml). After continuing stirring at rt for 2 h, DCM was removed on the rotavapour to obtain the titled compound (47.6 g), which was used in the next step without further purification.

후처리

  1. stirringAfter continuing stirring at rt for 2 h
  2. customDCM was removed on the rotavapour

출처 및 근거

ORD 기록
ord-6737c575ce5f456ba1fa5fc556be1d57
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181214B2

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