4-Phenylpiperidine → 1-(1-Naphthoxy)-3-(4-phenylpiperidino)-2-propanol

HRID 1834116Notes

Reaction equation

HRID 1834116 reaction equation
[O:1]1[CH:3]([CH2:4][O:5][C:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][CH:7]=2)[CH2:2]1.[C:16]1([CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[C:6]1([O:5][CH2:4][CH:3]([OH:1])[CH2:2][N:25]2[CH2:26][CH2:27][CH:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:23][CH2:24]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 698734-PhenylpiperidineHCID 915212-((1-Naphthalenyloxy)methyl)oxirane

Product 1

HCID 203742071-(1-Naphthoxy)-3-(4-phenylpiperidino)-2-propanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5.0 parts of 1,2-epoxy-3-(1-naphthoxy)propane in 79 parts of ethanol is added 5.0 parts of 4-phenylpiperidine. The resulting mixture is then refluxed for 24 hours. Evaporation of the solvent from the reaction mixture under reduced pressure affords 1-(1-naphthoxy)-3-(4-phenylpiperidino)-2-propanol. This free amine is then dissolved in isopropanol and treated with a solution of hydrochloric acid in isopropanol. The resulting salt is separated by filtration and recrystallized from a mixture of ethanol and ethyl ether to give 1-(1-naphthoxy)-3-(4-phenylpiperidino)-2-propanol hydrochloride. This compound melts at 195°-197° C. and is represented by the following structural formula ##STR6##

Workup

  1. temperatureThe resulting mixture is then refluxed for 24 hours
  2. customEvaporation of the solvent from the reaction mixture under reduced pressure

Sources & evidence

ORD record
ord-f7193c4747b846098338e2cfa59ffbf0
Source dataset
uspto-grants-1978_01
Patent number
US04069221

Reaction notes

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