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

HRID 710084ノート

反応式

HRID 710084 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-6737c575ce5f456ba1fa5fc556be1d57
出典データセット
uspto-grants-2015_11
特許番号
US09181214B2

反応ノート

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