Benzene, (3-bromopropoxy)- → N-(3-Phenoxypropyl)-1,1-dimethyl-2-(4-methoxyphenyl)ethylamine Hydrochloride

HRID 1270614Notes

Reaction equation

HRID 1270614 reaction equation
[CH3:1][C:2]([NH2:13])([CH3:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.[O:14]([CH2:21][CH2:22][CH2:23]Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[ClH:25].CO>C(#N)C>[ClH:25].[O:14]([CH2:21][CH2:22][CH2:23][NH:13][C:2]([CH3:1])([CH3:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 68522Benzene, (3-bromopropoxy)-HCID 918922-(4-Methoxyphenyl)-1,1-dimethylethylamineHCID 21893726Hydrochloride methanol

Product 1

HCID 22640941N-(3-Phenoxypropyl)-1,1-dimethyl-2-(4-methoxyphenyl)ethylamine Hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of 50% KF-Celite (0.35 g, 3 mmol) in anhydrous acetonitrile (10 mL) was added 1,1-dimethyl-2-(4-methoxyphenyl)ethylamine (0.27 g, 1.5 mmol) and 3-phenoxypropyl bromide (0.484 g, 2.25 mmol). The reaction mixture was refluxed under nitrogen for 6 hours, followed by stirring at room temperature for 62 hours. The mixture was filtered and the filtrate, was evaporated. The hydrochloride was prepared by dissolving the residue in HCl/methanol. The resulting solution was concentrated and dried on a lyophilizer. The residue was redissolved in dry methanol and diluted with diethyl ether, which caused precipitation of 210 mg of the title compound as a white solid: GC/EI-MS, m/z (rel. int.) 298 (M−15, 2), 193 (15), 192 (100), 120 (13), 107 (5), 98 (9), 77 (8), 72 (7), 71 (8), 70 (6), 41 (4).

Workup

  1. temperatureThe reaction mixture was refluxed under nitrogen for 6 hours
  2. filtrationThe mixture was filtered
  3. customthe filtrate, was evaporated
  4. concentrationThe resulting solution was concentrated
  5. customdried on a lyophilizer
  6. dissolutionThe residue was redissolved in dry methanol
  7. additiondiluted with diethyl ether, which
  8. customprecipitation of 210 mg of the title compound as a white solid

Sources & evidence

ORD record
ord-df512d1a0dab4817aecbb35fa622ec92
Source dataset
uspto-grants-2007_04
Patent number
US07202261B2

Reaction notes

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