Ethanol → 4-amino-N-(1-methylpiperidin-4-yl)benzamide

HRID 2111301Notes

Reaction equation

HRID 2111301 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:19])[C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)[CH2:4][CH2:3]1.C(O)C>[Pd].O1CCCC1>[NH2:16][C:13]1[CH:12]=[CH:11][C:10]([C:9]([NH:8][CH:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[O:19])=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 10587627N-(1-methyl-piperidin-4-yl)-4-nitro-benzamide

Product 1

HCID 433732804-amino-N-(1-methylpiperidin-4-yl)benzamideYield 57.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.34 g (0.0165 mole) of N-(1-methyl-piperidin-4-yl)-4-nitro-benzamide, 0.50 g of 10% palladium on carbon catalyst, 200 mL of ethanol and 30 mL of tetrahydrofuran was stirred under an atmosphere of hydrogen for 4 hours. The mixture was then filtered through Celite and concentrated under reduced pressure. The residue was recrystallized from methanol-ethyl acetate to give 2.21 g of 4-amino-N-(1-methyl-piperidin-4-yl)-benzamide as off-white crystals.

Workup

  1. filtrationThe mixture was then filtered through Celite
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was recrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-374db88d141549a59a3aaa343c273bc1
Source dataset
uspto-grants-2009_04
Patent number
US07517873B2

Reaction notes

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