Benzophenone imine → 3-(Benzhydrylideneamino)-piperidin-2-one

HRID 626902Notes

Reaction equation

HRID 626902 reaction equation
[C:1](=[NH:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N[CH:16]1[CH2:21][CH2:20][CH2:19][NH:18][C:17]1=[O:22]>ClCCCl>[C:1](=[N:14][CH:16]1[CH2:21][CH2:20][CH2:19][NH:18][C:17]1=[O:22])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 136809Benzophenone imineHCID 52002253-Amino-2-piperidone

Product 1

HCID 900151013-(Benzhydrylideneamino)-piperidin-2-oneYield 78.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

Benzophenone imine (3 mL, 17.87 mmol) was added to a solution of 3-aminopiperidin-2-one [CAS 1892-22-4] (2 g, 17.52 mmol) and molecular sieves in DCE (50 mL) under nitrogen and the reaction was warmed to 80° C. for 18 hours. The solvent was evaporated and the residue applied to a 100 g SNAP column, eluting with 50 to 100% EtOAc/ihexane to afford 3-(benzhydrylideneamino)-piperidin-2-one (D21) (3.84 g, 13.796 mmol, 78.7% yield) as a colourless solid.

Workup

  1. customThe solvent was evaporated
  2. washeluting with 50 to 100% EtOAc/ihexane

Sources & evidence

ORD record
ord-e75b8912d44c45b7ad0b96902d5aa5b7
Source dataset
uspto-grants-2016_04
Patent number
US09309254B2

Reaction notes

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