4-(4-Chlorophenyl)-4-hydroxypiperidine → HCID 14368938, compound

HRID 1073497Notes

Reaction equation

HRID 1073497 reaction equation
CS(O[CH2:6][CH:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH2:8]1)(=O)=O.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2([OH:34])[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:24][CH:23]=1>CN(C=O)C>[CH3:20][O:19][C:16]1[CH:15]=[CH:14][C:13]([N:9]2[CH2:8][CH:7]([CH2:6][N:31]3[CH2:30][CH2:29][C:28]([C:25]4[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=4)([OH:34])[CH2:33][CH2:32]3)[O:11][C:10]2=[O:12])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 10870338HCID 10870338, compound

Product 1

HCID 14368938HCID 14368938, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.82 g of 5-methanesulfonyloxymethyl-3-p-methoxyphenyl-oxazolidin-2-one [m.p. 126°-128°; obtainable by reaction of p-methoxyaniline with hydroxymethyl-oxirane to give 3-p-methoxyanilino-1,2-propanediol, reaction with diethyl carbonate to give 3-p-methoxyphenyl-5-hydroxymethyl-oxazolidin-2-one (m.p. 133°-134°) and reaction with CH3SO2Cl] is heated together with 5.08 g of 4-p-chlorophenyl-4-hydroxypiperidine in 25 ml of DMF at 95°-100° for 1 hour; the mixture is cooled and worked up in a conventional manner to give 3-p-methoxyphenyl-5-(4-p-chlorophenyl-4-hydroxy-piperidinomethyl)-oxazolidin-2-one, m.p. 143°-144°.

Workup

  1. temperaturethe mixture is cooled

Sources & evidence

ORD record
ord-99528400a9ee48f0903c3bf741e1ee43
Source dataset
uspto-grants-1990_11
Patent number
US04970217

Reaction notes

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