Hydrochloric Acid → 4,4-Difluorocyclohexan-1-amine hydrochloride

HRID 490915

Reaction equation

HRID 490915 reaction equation
[ClH:1].CC([N:6]([CH:10]1[CH2:15][CH2:14][C:13]([F:17])([F:16])[CH2:12][CH2:11]1)C(=O)[O-])(C)C>O1CCOCC1>[ClH:1].[F:16][C:13]1([F:17])[CH2:14][CH2:15][CH:10]([NH2:6])[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866089811,1-Dimethylethyl(4,4-difluorocyclohexyl)carbamate

Product 1

HCID 231506694,4-Difluorocyclohexan-1-amine hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of hydrogen chloride in dioxane (4M, 1.6 ml) was added at 20° C. to a stirred solution of Intermediate 146 (140 mg, 0.6 mmol), in dioxane (1.6 ml). After 3 h, the reaction mixture was concentrated in vacuo to afford Intermediate 147 (96.5 mg) containing 4-fluoro-3-cyclohexen-1-amine. 1H NMR (400 MHz in d6-DMSO, 27° C., δ ppm) Minor component: δ8.22 (br, 3H excess), 5.18 (dm, 16 Hz, 1H), 3.28-3.13 (m, 1H excess), 2.41-1.53 (m's, 6H excess). Major component: δ8.22 (br, 3H excess), 3.28-3.13 (m, 1H excess), 2.41-1.53 (m's, 8H excess). Impurities are also present.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-0e40c39914874464865b8c3367e3f417
Source dataset
uspto-grants-2009_05
Patent number
US07528148B2

Linked notes

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