2-((1-Naphthalenyloxy)methyl)oxirane → 3-[4-(p-Chlorophenyl)-4-ethoxycarbonylpiperidino]-1-(1-naphthoxy)-2-propanol

HRID 1834118Notes

Reaction equation

HRID 1834118 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.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:19][CH:18]=1>C(O)C>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:24][CH2:25][N:26]([CH2:2][CH:3]([OH:1])[CH2:4][O:5][C:6]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH:9]=[CH:8][CH:7]=3)[CH2:27][CH2:28]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 915212-((1-Naphthalenyloxy)methyl)oxiraneHCID 187941774-(4-Chlorophenyl)piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 203741993-[4-(p-Chlorophenyl)-4-ethoxycarbonylpiperidino]-1-(1-naphthoxy)-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-(p-chlorophenyl)-4-ethoxycarbonylpiperidine. The resulting mixture is then refluxed for 24 hours. The solvent is stripped from the reaction mixture under reduced pressure to afford 3-[4-(p-chlorophenyl)-4-ethoxycarbonylpiperidino]-1-(1-naphthoxy)-2-propanol. This material is 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 isopropanol and ethyl ether to give 3-[4-(p-chlorophenyl)-4-ethoxycarbonylpiperidino]-1-(1-naphthoxy)-2-propanol hydrochloride. This compound exhibits a melting point of 196°-198° C. and is represented by the following structural formula ##STR8##

Workup

  1. temperatureThe resulting mixture is then refluxed for 24 hours

Sources & evidence

ORD record
ord-7a5611517da2482fa2e4b0bb01f15ab2
Source dataset
uspto-grants-1978_01
Patent number
US04069221

Reaction notes

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