Ammonium Hydroxide → cis-2-Aminocyclohexanecarboxamide

HRID 7024

Reaction equation

HRID 7024 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@@H:6]1[NH2:11])=O.[OH-].[NH4+:13]>C1(C)C=CC=CC=1>[NH2:11][C@H:6]1[CH2:7][CH2:8][CH2:9][CH2:10][C@H:5]1[C:3]([NH2:13])=[O:2]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 24751169methyl (1R,2S)-2-aminocyclohexanecarboxylate

Product 1

HCID 2724813cis-2-Aminocyclohexanecarboxamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

cis-2-Aminocyclohexanecarboxylic acid methyl ester (2.20 g, 14.0 mmol) was treated with aqueous ammonium hydroxide (40 mL) in toluene (40 mL) and stirred vigorously at room temperature for 16 h. The reaction was concentrated to dryness in vacuo and azeotroped with toluene (50 mL). The crude product, cis-2-aminocyclohexanecarboxylic acid amide, was used in the next reaction without purification: 1H NMR (400 MHz, DMSO-d6) δ 7.78 (2 H, s br), 7.67 (s, 1 H), 7.25 (s, 1 H), 1.87 (m, 2 H), 1.60 (m, 4 H), 1.41 (m, 4 H).

Workup

  1. concentrationThe reaction was concentrated to dryness in vacuo
  2. customazeotroped with toluene (50 mL)
  3. customThe crude product, cis-2-aminocyclohexanecarboxylic acid amide, was used in the next reaction without purification

Sources & evidence

ORD record
ord-fc1c3c23629140928ac9e042705804cc
Source dataset
uspto-grants-2006_08
Patent number
US07084178B2

Linked notes

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