Hydrochloric Acid → HCID 68673998, compound

HRID 333247Notes

Reaction equation

HRID 333247 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]([C:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=O.[ClH:18].CCOC(C)=O>CC#N>[ClH:18].[CH3:1][N:2]([CH3:17])[CH2:3][C:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 8857Ethyl AcetateHCID 68673885HCID 68673885, compound

Product 1

HCID 68673998HCID 68673998, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was synthesized from N,N-dimethyl-1-phenylcyclohexanecarboxamide (200 mg, 0.87 mmol) using General Procedure E, followed by HCl salt formation. The crude HCl salt was rechrystallized from 2:1 EtOAc:CH3CN to give N,N-dimethyl(1-phenylcyclohexyl)methanamine hydrochloride as an analytically pure off-white solid (8 mg, 4%). HPLC Rt=8.55 min; 1H NMR (400 mHz, MeOH-d4) 7.30 (q, 4H), 2.30 (s, 2H), 2.09-2.06 (m, 2H), 1.97 (s, 6H), 1.60-1.25 (m, 10H); LC-MS 8.09 min, (M+1)+ 252 @ 8.15 min. HPLC Rt=8.03 min; 1H NMR (400 mHz, MeOH-d4) 7.48-7.39 (m, 4H), 7.29-7.28 (m, 1H), 3.34 (d, J=2.57 Hz, 2H), 2.46 (d, J=3.30 Hz, 6H), 2.29-2.26 (m, 2H), 1.67-1.39 (m, 8H); LC-MS 6.62 min, (M+1)+ 218 @ 6.80 min.

Sources & evidence

ORD record
ord-85623ea701b3422a823a5e4bda5b1733
Source dataset
uspto-grants-2014_11
Patent number
US08877975B2

Reaction notes

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