Ethanol → 2-(4-Phenyl-4-hydroxypiperidinomethyl)-6,7-dimethoxy-1-tetralone hydrochloride

HRID 328254Notes

Reaction equation

HRID 328254 reaction equation
[ClH:1].[C:2]1([C:8]2([OH:14])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:26]=1[O:27][CH3:28])[C:23](=[O:29])[CH2:22][CH2:21][CH2:20]2.C=O.[CH2:32](O)C>C(O)(C)C>[ClH:1].[C:2]1([C:8]2([OH:14])[CH2:13][CH2:12][N:11]([CH2:32][CH:22]3[CH2:21][CH2:20][C:19]4[C:24](=[CH:25][C:26]([O:27][CH3:28])=[C:17]([O:16][CH3:15])[CH:18]=4)[C:23]3=[O:29])[CH2:10][CH2:9]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 712FormaldehydeHCID 2668163,4-Dihydro-6,7-dimethoxy-1(2H)-naphthalenoneHCID 186143834-Phenylpiperidin-4-ol hydrochloride

Product 1

HCID 69179102-(4-Phenyl-4-hydroxypiperidinomethyl)-6,7-dimethoxy-1-tetralone hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 21.35 g. of 4-phenylpiperidin-4-ol hydrochloride, 20.6 g. of 6,7-dimethoxy-1-tetralone and 8 g. of paraformaldehyde in 200 ml. of ethanol (or isopropanol) is heated under reflux for 4 hours. The solvent is evaporated and the residue is made into a slurry with acetone/ether and is filtered off. 2-(4-phenyl-4-hydroxypiperidinomethyl)-6,7-dimethoxy-1-tetralone hydrochloride, m.p. 175°-177°, is obtained.

Workup

  1. additionA mixture of 21.35 g
  2. temperatureunder reflux for 4 hours
  3. customThe solvent is evaporated
  4. filtrationis filtered off

Sources & evidence

ORD record
ord-c1956a658f884b62a58ca734348e8e33
Source dataset
uspto-grants-1977_04
Patent number
US04016281

Reaction notes

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