Methanol → N-[2-Hydroxy-3-(1-naphthoxy)propyl]-1,1-dimethyl-2-(4-fluorophenyl)ethylamine Hydrochloride

HRID 2302145Notes

Reaction equation

HRID 2302145 reaction equation
[CH2:1]([O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1)[CH:2]1[O:4][CH2:3]1.[CH3:16][C:17]([NH2:27])([CH3:26])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1.CO.C(Cl)(Cl)[Cl:31]>C(O)C>[ClH:31].[OH:4][CH:2]([CH2:1][O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1)[CH2:3][NH:27][C:17]([CH3:26])([CH3:16])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6212Chloroform2×HCID 915212-((1-Naphthalenyloxy)methyl)oxiraneHCID 5184711-(4-Fluorophenyl)-2-methyl-2-aminopropane

Product 1

HCID 18459602N-[2-Hydroxy-3-(1-naphthoxy)propyl]-1,1-dimethyl-2-(4-fluorophenyl)ethylamine Hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 1-naphthyl glycidyl ether (400 mg, 2 mmol) and 1,1-dimethyl-2-(4-fluorophenyl)ethylamine (334 mg, 2 mmol) in absolute ethanol (2 mL) was heated at 50-60° C. for 16 hours. Chromatography of the resulting reaction mixture through silica (5×30 cm) using a gradient of chloroform to 5% methanol in chloroform afforded the free base of the title compound: GC/EI-MS, m/z (rel. int.) 368 (M+1, 1), 352 (2), 258 (100), 183 (5), 157 (4), 127 (5), 115 (18), 109 (23), 71 (30).

Workup

  1. customChromatography of the resulting reaction mixture through silica (5×30 cm)

Sources & evidence

ORD record
ord-db0315e7d96b479d8be09da65c5a955a
Source dataset
uspto-grants-2002_08
Patent number
US06432656B1

Reaction notes

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