Benzenamine hydrochloride (1:1) → N-Phenylcyclohexanecarboxamide

HRID 1733867Notes

Reaction equation

HRID 1733867 reaction equation
[CH:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)C(C)C)(C)C>ClCCl>[C:12]1([NH:11][C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:8])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 8870Benzenamine hydrochloride (1:1)HCID 75938Cyclohexanecarbonyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 257030N-PhenylcyclohexanecarboxamideYield 91.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyclohexanecarbonyl chloride (14.66 g, 0.1 mol) was added dropwise to a stirred solution of aniline hydrochloride (12.96 g 0.1 mol) and N, N-diisopropylethylamine (15.20 g, 0.2 mol) in dichloromethane (100 ml). The solution was stirred under an atmosphere of argon for 18 h, washed with 0.1 N-HC1 (3×50 ml) and dilute sodium hydrogen carbonate solution (50 ml), dried (MgSO4), and evaporated in vacuo to give the product (18.6 g) as white crystals.

Workup

  1. washwashed with 0.1 N-HC1 (3×50 ml) and dilute sodium hydrogen carbonate solution (50 ml)
  2. dry with materialdried (MgSO4)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-509746ea222e4554990b76ad038f14ee
Source dataset
uspto-grants-1996_07
Patent number
US05532242

Reaction notes

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