4-Nitrobenzoyl chloride → 3-Dimethylamino-1-(4-nitrobenzoyl)pyrrolidine

HRID 1176057Notes

Reaction equation

HRID 1176057 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(C(C)C)CC)(C)C.[CH3:22][N:23]([CH3:29])[CH:24]1[CH2:28][CH2:27][NH:26][CH2:25]1>C1COCC1>[CH3:22][N:23]([CH3:29])[CH:24]1[CH2:28][CH2:27][N:26]([C:8](=[O:9])[C:7]2[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:25]1

Participants

5

Reactant 3

HCID 85024-Nitrobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 27585193-(Dimethylamino)pyrrolidine

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-nitrobenzoyl chloride (1.8 g, 10 mmol) and diisopropylethylamine (2.8 mL, 20 mmol) in THF at room temperature is added 3-(dimethylamino)pyrrolidine (1.4 mL, 11 mmol). The reaction is stirred for 2 hours at room temperature and concentrated in vacuo to give 3-dimethylamino-1-(4-nitrobenzoyl)pyrrolidine, identified by HPLC and MS [264.3 m/e (M+H)] analyses.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-79817f0eddc4467bbdc7f2664c61feff
Source dataset
uspto-grants-2010_11
Patent number
US07842715B2

Reaction notes

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