Hydrazine → 1-(4-Aminobenzoyl)-3-dimethylamino-pyrrolidine

HRID 1176058Notes

Reaction equation

HRID 1176058 reaction equation
[CH3:1][N:2]([CH3:19])[CH:3]1[CH2:7][CH2:6][N:5]([C:8](=[O:18])[C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[CH2:4]1.NN>CO.[Ni]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([C:8]([N:5]2[CH2:6][CH2:7][CH:3]([N:2]([CH3:1])[CH3:19])[CH2:4]2)=[O:18])=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 225675623-Dimethylamino-1-(4-nitrobenzoyl)pyrrolidine

Product 1

HCID 225674711-(4-Aminobenzoyl)-3-dimethylamino-pyrrolidine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

The 3-dimethylamino-1-(4-nitrobenzoyl)pyrrolidine (2.4 g, crude), obtained in Step 1, is dissolved in methanol, treated sequentially with hydrazine (5 mL) and Raney-Nickel (suspension in water, approximately 1 g), stirred at room temperature for 4 h and filtered through celite. The filtercake is washed with methanol. The filtrates are combined and concentrated to give 1-(4-aminobenzoyl)-3-dimethylamino-pyrrolidine as a pale brown oil, identified by HPLC and MS [234.5 m/e (M+H)].

Workup

  1. filtrationfiltered through celite
  2. washThe filtercake is washed with methanol
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-35e8b44c40304af5812e7decb0c86492
Source dataset
uspto-grants-2010_11
Patent number
US07842715B2

Reaction notes

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