Hydrochloric Acid → n-(2-Hydroxy-3phenoxypropyl)-1,1-dimethyl-2-phenylethylamine hydrochloride

HRID 1270622Notes

Reaction equation

HRID 1270622 reaction equation
[ClH:1].[OH:2][CH:3]([CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23](OC)=[CH:22][CH:21]=1)[CH2:4][NH:5][C:6]([CH3:17])([CH3:16])[CH2:7][C:8]1[CH:13]=[CH:12][C:11](OC)=[CH:10][CH:9]=1.Cl>C(OCC)C>[ClH:1].[OH:2][CH:3]([CH2:18][O:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:4][NH:5][C:6]([CH3:17])([CH3:16])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22640899N-[2-Hydroxy-3-(4-methoxyphenoxy)propyl]-1,1-dimethyl-2-(4-methoxyphenyl)ethylamine Hydrochloride

Product 1

HCID 22640946n-(2-Hydroxy-3phenoxypropyl)-1,1-dimethyl-2-phenylethylamine hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Using the method of Example 5, supra, 1,2-epoxy-3-phenoxypropane (600 mg, 4 mmol) and 1,1-dimethyl-2-phenylethylamine (596 mg, 4 mmol) yielded the title compound: GC/EI-MS, m/z (rel. int.) 284 (M+1, 1), 208 (100), 162 (1), 133 (7), 91 (27), 77 (15), 70 (22). The free base in diethyl ether was treated with excess 1M HCl (diethyl ether). The resulting solid was recrystallized from hot acetonitrile to afford 596 mg of the hydrochloride product as a white solid.

Workup

  1. customThe resulting solid was recrystallized from hot acetonitrile

Sources & evidence

ORD record
ord-ebb7bad954374860adee4a53c4d5a95b
Source dataset
uspto-grants-2007_04
Patent number
US07202261B2

Reaction notes

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