Hydrochloric Acid → HCID 68673057, compound

HRID 333245Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:9]2([C:15]([N:17]([CH3:19])[CH3:18])=O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[ClH:20]>>[ClH:20].[F:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:15][N:17]([CH3:19])[CH3:18])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 68675491HCID 68675491, compound

Product 1

HCID 68673057HCID 68673057, compoundYield 8%

Procedure

The title compound was synthesized from 1-(3,4-difluorophenyl)-N,N-dimethylcyclohexanecarboxamide (195 mg, 0.73 mmol) using General Procedure E (the amide was prepared from the corresponding carboxylic acid according to General Procedure G), followed by HCl salt formation. The crude HCl salt was recrystallized from 1:1 CH3CN:EtOAc (3.0 mL) to give pure (1-(3,4-difluorophenyl)cyclohexyl)-N,N-dimethylmethanamine hydrochloride as an off-white solid (16 mg, 8%). HPLC Rt=8.24 min; 1H NMR (400 mHz, MeOH-d4) 7.51-7.46 (m, 1H), 7.37-7.34 (m, 2H), 3.31-3.30 (m, 2H), 2.62 (s, 6H), 2.26-2.23 (m, 2H), 1.78-1.38 (m, 8H); LC-MS 7.69 min, (M+1)+ 254 @ 791 min.

Workup

customThe crude HCl salt was recrystallized from 1:1 CH3CN

Sources & evidence

ORD record: ord-476cbd948b1a41999152e93140f511a4
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877975B2

Reaction notes

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