Hydrochloric Acid → HCID 22640915, compound

HRID 1060353Notes

Reaction equation

HRID 1060353 reaction equation
[ClH:1].[OH:2][CH:3]([CH2:17][O:18][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1)[CH2:4][NH:5][C:6]([CH3:16])([CH3:15])[CH2:7][C:8]1[CH:13]=[CH:12][C:11](F)=[CH:10][CH:9]=1.Cl.[OH:30][CH:31](COC1C=CC=CC=1)CNC(C)(C)CC1C=CC(OC)=CC=1.Cl>C(OCC)C>[ClH:1].[OH:2][CH:3]([CH2:17][O:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=1)[CH2:4][NH:5][C:6]([CH3:15])([CH3:16])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([O:30][CH3:31])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 18459602N-[2-Hydroxy-3-(1-naphthoxy)propyl]-1,1-dimethyl-2-(4-fluorophenyl)ethylamine HydrochlorideHCID 22640854n-(2-Hydroxy-3-phenoxypropyl)-1,1-dimethyl-2-(4-methoxyphenyl)ethylamine hydrochloride

Product 1

HCID 22640915HCID 22640915, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Using the method of Example 4, supra, 2-naphthyl glycidyl ether (400 mg, 2 mmol) and 1,1-dimethyl-2-(4-methoxyphenyl)ethylamine (358 mg, 2 mmol) were used to prepare the free base of the title compound: GC/EI-MS, m/z (rel. int.) 364 (M-15, 1), 258 (100), 183 (2), 163 (3), 144 (4), 127 (10), 121 (22), 115 (20), 71 (11). The free base in diethyl ether was treated with excess 1M HCl (diethyl ether). The resulting solid was recrystallized from hot acetonitrile to afford 496 mg of the hydrochloride product as a white solid.

Workup

  1. customThe resulting solid was recrystallized from hot acetonitrile

Sources & evidence

ORD record
ord-c696d22d07a340b8851162139c3dca37
Source dataset
uspto-grants-2003_02
Patent number
US06521667B1

Reaction notes

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