3-isopropoxy-N-(1-methyl-piperidin-4-yl)-4-nitro-benzamide → 4-amino-3-isopropoxy-N-(1-methyl-piperidin-4-yl)-benzamide

HRID 1676534Notes

Reaction equation

HRID 1676534 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:18]=[CH:19][C:20]=1[N+:21]([O-])=O)[C:8]([NH:10][CH:11]1[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]1)=[O:9])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[NH2:21][C:20]1[CH:19]=[CH:18][C:7]([C:8]([NH:10][CH:11]2[CH2:12][CH2:13][N:14]([CH3:17])[CH2:15][CH2:16]2)=[O:9])=[CH:6][C:5]=1[O:4][CH:1]([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 670764013-isopropoxy-N-(1-methyl-piperidin-4-yl)-4-nitro-benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 580149994-amino-3-isopropoxy-N-(1-methyl-piperidin-4-yl)-benzamideYield 95.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1.2 g (3.6 mmole) of 3-isopropoxy-N-(1-methyl-piperidin-4-yl)-4-nitro-benzamide in 25 mL of methanol was added 0.12 g of 10% palladium on carbon. The hydrogenation reaction was carried out under 50 psi of hydrogen for 2 hours. The mixture was filtered, concentrated under reduced pressure and triturated with ether. The solid was collected by filtration, washed with ether and dried under vacuum to give 1.0 g of 4-amino-3-isopropoxy-N-(1-methyl-piperidin-4-yl)-benzamide as a white solid.

Workup

  1. customThe hydrogenation reaction
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. customtriturated with ether
  5. filtrationThe solid was collected by filtration
  6. washwashed with ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-695d0ef61d084dc6ab4ef81caf607ec8
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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