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

HRID 362905Notes

Reaction equation

HRID 362905 reaction equation
[CH3:1][NH:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][CH2:5]1.[C:23]12[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=1)[NH:28]C(=O)[O:26][C:24]2=O.C([O-])(O)=O.[Na+]>CN(C)C1C=CN=CC=1.CN(C=O)C>[NH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:23]=1[C:24]([N:2]([CH3:1])[CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:6][CH2:5]1)=[O:26]

Participants

6

Reactant 3

HCID 8359Isatoic AnhydrideHCID 516892Sodium BicarbonateHCID 537192494-(N-methylamino)methyl-1-diphenylmethylpiperidine

Product 1

HCID 675951382-amino-N-methyl-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamideYield 67%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Step 3): A solution of 4-(N-methylamino)methyl-1-diphenylmethylpiperidine (1.8 g, 6.0 mmol), isatoic anhydride (0.9 g, 5.5 mmol) and 4-dimethylaminopyridine (0.74 g) in DMF (25 ml) was stirred at room temperature for 2 hours. The reaction mixture was poured into 1% NaHCO3 solution and extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate and hexane) to give 2-amino-N-methyl-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide (1.5 g, 67%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate and hexane)

Sources & evidence

ORD record
ord-04f806f826cd45c79ee9fdcb12f08b60
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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