2-((1-Naphthalenyloxy)methyl)oxirane → HCID 20374203, compound

HRID 1834117Notes

Reaction equation

HRID 1834117 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]([C:18]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)#[N:17]>C(O)C>[C:16]([C:18]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:19][CH2:20][N:21]([CH2:2][CH:3]([OH:1])[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)[CH2:22][CH2:23]1)#[N:17]

Participants

4

Reactant 2

HCID 915212-((1-Naphthalenyloxy)methyl)oxiraneHCID 1811384-Piperidinecarbonitrile, 4-phenyl-

Product 1

HCID 20374203HCID 20374203, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5.0 parts of 1,2-epoxy-3-(1-naphthoxy)-propane and 5.0 parts of 4-cyano-4-phenylpiperidine in 79 parts of ethanol is refluxed for 24 hours. Evaporation of the solvent from the reaction mixture under reduced pressure affords 3-(4-cyano-4-phenylpiperidino)-1-(1-naphthoxy)-2-propanol. The hydrochloride salt is then prepared by addition of a solution of hydrochloric acid in isopropanol to an isopropanol solution of the free amine. The resulting salt is separated by filtration and recrystallized from isopropanol to afford 3-(4-cyano-4-phenylpiperidino)-1-(1-naphthoxy)-2-propanol hydrochloride, melting at 213°-215° C. and represented by the following structural formula ##STR7##

Workup

  1. customEvaporation of the solvent from the reaction mixture under reduced pressure

Sources & evidence

ORD record
ord-fa23c35c3b7f4b899cbe08d0f37887ba
Source dataset
uspto-grants-1978_01
Patent number
US04069221

Reaction notes

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