Acetate-hydrochloric acid → 1-(4,4-Difluorocyclohexyl)methanamine hydrochloride

HRID 1435486Notes

Reaction equation

HRID 1435486 reaction equation
C(OC(=O)[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][C:12]([F:16])([F:15])[CH2:11][CH2:10]1)(C)(C)C.[ClH:18].CC(O)=O>>[ClH:18].[F:15][C:12]1([F:16])[CH2:13][CH2:14][CH:9]([CH2:8][NH2:7])[CH2:10][CH2:11]1

Participants

3

Reactant 2

HCID 22641269Acetate-hydrochloric acidHCID 57441078tert-Butyl ((4,4-difluorocyclohexyl)methyl)carbamate

Product 1

HCID 451589311-(4,4-Difluorocyclohexyl)methanamine hydrochloride

Procedure

tert-Butyl[(4,4-difluorocyclohexyl)methyl]carbamate (505 mg, 2.03 mmol) was stirred in 5 mL of 1M HCl/AcOH at rt for 2 h. The solvent was evaporated. The residue washed with ether, filtered and dried. Yield: 330 mg (88%); 1H NMR (400 MHz, CD3OD) δ 1.28-1.40 (m, 2 H), 1.71-1.82 (m, 2 H), 1.84 (d, J=3.12 Hz, 2 H), 1.86-1.89 (m, 1 H), 2.03-2.15 (m, 2 H), 2.85 (d, J=7.03 Hz, 2 H).

Workup

  1. customThe solvent was evaporated
  2. washThe residue washed with ether
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-7c86d21c201744189d91d22f19ce1b86
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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