Phthalimide → 1-(p-Chlorobenzyl)-3-phthalimidomethylpiperidine

HRID 1598371Notes

Reaction equation

HRID 1598371 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH2:10][CH:9]([CH2:13]O)[CH2:8]2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:36]1(=[O:46])[NH:40][C:39](=[O:41])[C:38]2=[CH:42][CH:43]=[CH:44][CH:45]=[C:37]12.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH2:10][CH:9]([CH2:13][N:40]3[C:39](=[O:41])[C:38]4=[CH:42][CH:43]=[CH:44][CH:45]=[C:37]4[C:36]3=[O:46])[CH2:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18933403[1-(4-Chloro-benzyl)-piperidin-3-yl]-methanol

Product 1

HCID 189334311-(p-Chlorobenzyl)-3-phthalimidomethylpiperidineYield 150.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(p-chlorobenzyl)-3-hydroxymethyl piperidine (4.0 g, 19 mmol) in THF (40 ml) were added successively triphenylphosphine (5.60 g, 21.3 mmol), phthalimide (3.14 g, 21.4 mmol) and diethyl azodicarboxylate (3.4 ml, 21 mmol) under ice-cooling and the mixture was stirred for 1.5 hours. The solvent was distilled off from the reaction mixture under reduced pressure to give 10.52 g of crude 1-(p-chlorobenzyl)-3-phthalimidomethylpiperidine. This compound was used for the subsequent reaction without purification.

Workup

  1. temperaturecooling
  2. distillationThe solvent was distilled off from the reaction mixture under reduced pressure

Sources & evidence

ORD record
ord-75276c98b8944b3dbc508a1b28eaaef7
Source dataset
uspto-grants-1998_04
Patent number
US05736550

Reaction notes

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