Dimethylamine → HCID 53745368, compound

HRID 362899Notes

Reaction equation

HRID 362899 reaction equation
Cl[C:2]1[C:3]([N+:30]([O-:32])=[O:31])=[C:4]([CH:27]=[CH:28][CH:29]=1)[C:5]([NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:6].[CH3:33][NH:34][CH3:35].O>CN(C=O)C>[CH3:33][N:34]([CH3:35])[C:2]1[C:3]([N+:30]([O-:32])=[O:31])=[C:4]([CH:27]=[CH:28][CH:29]=1)[C:5]([NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:6]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 54410326HCID 54410326, compound

Product 1

HCID 53745368HCID 53745368, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Step 2): A solution of 3-chloro-2-nitro-N-(1-diphenylmethylpiperidin-4-yl)benzamide (13.5 g, 30 mmol) and 40% dimethylamine (20 ml) in DMF (60 ml) was heated at 130° C. for 15.5 hours in a sealed tube. The mixture was poured into water and extracted with ether. The organic layer was washed with water, dried (MgSO4) and concentrated. The residue was recrystallized (ethyl acetate/hexane) to give 3-dimethylamino-2-nitro-N-(1-diphenylmethyl piperidin-4-yl)benzamide (88.5%): mp 176° C.

Workup

  1. extractionextracted with ether
  2. washThe organic layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was recrystallized (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4df8c1c8bcdd49cfb8ab380e45060d64
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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