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

HRID 710084Notes

Reaction equation

HRID 710084 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-6737c575ce5f456ba1fa5fc556be1d57
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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