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

HRID 2302158Notes

Reaction equation

HRID 2302158 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.OC(COC(C)C)CNC(C)(C)CC1C=CC(OC)=CC=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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 22640899N-[2-Hydroxy-3-(4-methoxyphenoxy)propyl]-1,1-dimethyl-2-(4-methoxyphenyl)ethylamine HydrochlorideHCID 22640903N-(2-Hydroxy-3-isopropoxypropyl)-1,1-dimethyl-2-(4-methoxyphenyl)ethylamine

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-7f86791ab91341ceb7ce1c788110b7c0
Source dataset
uspto-grants-2002_08
Patent number
US06432656B1

Reaction notes

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