Hydrochloric Acid → HCID 68675471, compound

HRID 333244Notes

Reaction equation

HRID 333244 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([C:14]([N:16]([CH3:18])[CH3:17])=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Cl>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:14][N:16]([CH3:18])[CH3:17])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 68673352HCID 68673352, compound

Product 1

HCID 68675471HCID 68675471, compoundYield 20.2%

Procedure

The title compound was synthesized from 1-(3-chlorophenyl)-N,N-dimethylcyclohexanecarboxamide (191 mg, 0.72 mmol) using General Procedure E, followed by HCl salt formation. The crude HCl salt was recrystallized from 2:1 CH3CN:EtOAc (4.5 mL) to give pure (1-(3-chlorophenyl)cyclohexyl)-N,N-dimethylmethanamine hydrochloride as an off-white solid (21 mg, 12%). HPLC Rt=8.41 min; 1H NMR (400 mHz, MeOH-d4) 7.51-7.30 (m, 4H), 3.26-3.24 (m, 2H), 2.54 (s, 6H), 2.24-2.20 (m, 2H), 1.72-1.33 (m, 8h); LC-MS 8.16 min, (M+1)− 252 @ 8.27 min.

Workup

  1. customThe crude HCl salt was recrystallized from 2:1 CH3CN

Sources & evidence

ORD record
ord-25abfee56efb4353ae6469fcf8c3f925
Source dataset
uspto-grants-2014_11
Patent number
US08877975B2

Reaction notes

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