Hydrochloric Acid → N-methyl-(1-phenylcyclohexyl)methanamine hydrochloride

HRID 333242Notes

Reaction equation

HRID 333242 reaction equation
[C:1]1([C:7]2([CH:13]=O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][NH2:16].[ClH:17]>>[CH3:15][NH:16][CH2:13][C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[ClH:17].[CH3:15][NH:16][CH2:13][C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 149226061-Phenylcyclohexane-1-carbaldehyde

Product 2

HCID 20803212N-methyl-(1-phenylcyclohexyl)methanamineHCID 68674577N-methyl-(1-phenylcyclohexyl)methanamine hydrochlorideYield 6%

Procedure

The title compound was synthesized from 1-phenylcyclohexane-carbaldehyde (126 mg, 0.67 mmol) and methyl amine (370 μL, 0.73 mmol, 2.0 M in THF) according to General Procedure H, followed by HCl salt formation. The HCl salt was recrystallized from CH3CN to give pure N-methyl(1-phenylcyclohexyl)methanamine hydrochloride (8 mg, 6%) as colorless crystals. HPLC Rt=7.76 min; 1H NMR (400 mHz, MeOH-d4) 7.43-7.38 (m, 4H), 7.28-7.25 (m, 1H), 3.11 (s, 2H), 2.50 (s, 3H), 2.25-2.22 (m, 2H), 1.67-1.23 (m, 8H); LC-MS 6.37 min, (M+1)+ 204 @ 6.62 min.

Workup

  1. customThe HCl salt was recrystallized from CH3CN

Sources & evidence

ORD record
ord-b1fb422ce6cd4e68a85721b51bc0429f
Source dataset
uspto-grants-2014_11
Patent number
US08877975B2

Reaction notes

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