Ethyl chloroformate → 4-Piperidinol, 4-[2-(hydroxymethyl)phenyl]-1-methyl-

HRID 1657847Notes

Reaction equation

HRID 1657847 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[O:14]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OCC)=O.C(OC(N1CCC2(C3C(=CC=CC=3)C(=O)O2)CC1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1C=CC=CC=1>[OH:14][C:11]1([C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:15][OH:22])[CH2:12][CH2:13][N:8]([CH3:1])[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 10928Ethyl chloroformateHCID 102664061'-Benzyl-3H-spiro[isobenzofuran-1,4'-piperidin]-3-oneHCID 21226445Aluminium lithium hydrideHCID 215068521,3-Dihydro-1'-ethoxycarbonylspiro[isobenzofuran-1,4'-piperidine]-3-one

Product 1

HCID 122896584-Piperidinol, 4-[2-(hydroxymethyl)phenyl]-1-methyl-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 5.8 g. of 1'-benzyl-1,3-dihydrospiro[isobenzofuran-1,4'-piperidine]-3-one, 40 ml. of benzene, and 2.5 ml. of ethyl chloroformate is heated under reflux for 18 hours and concentrated to a solid. Recrystallization from benzene-cyclohexane provides colorless crystals, m.p. 150°-151°, of 1,3-dihydro-1'-ethoxycarbonylspiro[isobenzofuran-1,4'-piperidine]-3-one. Reduction with lithium aluminum hydride by the method described in Example 16b provides 4-hydroxy-4-(α-hydroxy-2-tolyl)-1-methylpiperidine, m.p. 118°-119°.

Workup

  1. temperatureunder reflux for 18 hours
  2. concentrationconcentrated to a solid
  3. customRecrystallization from benzene-cyclohexane
  4. customprovides colorless crystals, m.p. 150°-151°

Sources & evidence

ORD record
ord-d9fa2d2bb481410da8244a61d923bdb4
Source dataset
uspto-grants-1976_06
Patent number
US03962259

Reaction notes

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