Hydrochloric Acid → Acetamide, N-(4-aminocyclohexyl)-, hydrochloride (1:1)

HRID 2386674Notes

Reaction equation

HRID 2386674 reaction equation
[ClH:1].C(OC(=O)[NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:16](=[O:18])[CH3:17])[CH2:11][CH2:10]1)(C)(C)C>CO>[ClH:1].[NH2:8][CH:9]1[CH2:10][CH2:11][CH:12]([NH:15][C:16](=[O:18])[CH3:17])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 66955585tert-Butyl (1R*,4R*)-4-acetamidocyclohexylcarbamate

Product 1

HCID 66728468Acetamide, N-(4-aminocyclohexyl)-, hydrochloride (1:1)

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

HCl (2.0 M in MeOH, 200 mL) was added to a suspension of (4-acetylamino-cyclohexyl)-carbamic acid tert-butyl ester (14.3 g) in MeOH (100 mL) and the resulting mixture was stirred at RT for 18 h. A second aliquot of HCl (2.0 M in MeOH, 100 mL) was then added and the resulting mixture was stirred at RT overnight. The reaction mixture was then concentrated under reduced pressure and the residue was triturated with Et2O. The very hygroscopic solid was collected by filtration after treatment with toluene, was then dried at 50° C. under reduced pressure to afford 12.46 g of N-(4-amino-cyclohexyl)-acetamide hydrochloride.

Workup

  1. stirringthe resulting mixture was stirred at RT overnight
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. customthe residue was triturated with Et2O
  4. filtrationThe very hygroscopic solid was collected by filtration after treatment with toluene
  5. customwas then dried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-4bcafc2f75bd4f08b554ff419407b961
Source dataset
uspto-grants-2012_09
Patent number
US08268840B2

Reaction notes

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