Chloroform → 2-amino-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

HRID 362902Notes

Reaction equation

HRID 362902 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:4]1.[C:22]12[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=1)[NH:27]C(=O)O[C:23]2=[O:24].C(Cl)(Cl)Cl>ClCCl>[NH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:22]=1[C:23]([NH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:5][CH2:4]1)=[O:24]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 8359Isatoic AnhydrideHCID 537860464-Aminomethyl-1-diphenylmethylpiperidine

Product 1

HCID 675948192-amino-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-aminomethyl-1-diphenylmethylpiperidine (2.5 g, 9.15 mmol) in dichloromethane (10 ml) was added to a suspension of isatoic anhydride (1.0 g, 6.1 mmol) in dichloromethane (25 ml) at room temperature. The reaction mixture was stirred for 1 hour and then poured into chloroform and washed with 5% NaHCO3 solution. The organic layer was concentrated. The residue was dissolved in dichloromethane (25 ml) and poured into hexane (400 ml) to give 2-amino-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide as precipitate (100%): mp 153°-154° C.

Workup

  1. washwashed with 5% NaHCO3 solution
  2. concentrationThe organic layer was concentrated
  3. dissolutionThe residue was dissolved in dichloromethane (25 ml)
  4. additionpoured into hexane (400 ml)

Sources & evidence

ORD record
ord-21eed670ff024463a2b3dfb82b4f5f51
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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