Pyrrolidine → N-(3-nitrophenyl)pyrrolidine-1-carboxamide

HRID 1852409Notes

Reaction equation

HRID 1852409 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:6]([C:9]1[CH:10]=[C:11]([N:15]=[C:16]=[O:17])[CH:12]=[CH:13][CH:14]=1)([O-:8])=[O:7]>C1COCC1>[N+:6]([C:9]1[CH:10]=[C:11]([NH:15][C:16]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:17])[CH:12]=[CH:13][CH:14]=1)([O-:8])=[O:7]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 768353-Nitrophenyl isocyanate

Product 1

HCID 350596N-(3-nitrophenyl)pyrrolidine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Pyrrolidine (1.5 mL, 18.3 mmol) was added to a stirred solution of 3-nitrophenyl isocyanate (1.5 g, 9.14 mmol) in anhydrous THF (60 mL) and the mixture stirred at reflux for 1 hour. The solvent was evaporated in vacuo. The crude product was then purified by column chromatography (Flashmaster, 40-63 mesh silica gel, 50% isohexane-EtOAc) to provide the title compound as an off white solid (1.85 g, 86%); LC-MS, Rt=2.80 min (MeOH-FA), m/z 236 (MH+).

Workup

  1. temperatureat reflux for 1 hour
  2. customThe solvent was evaporated in vacuo
  3. customThe crude product was then purified by column chromatography (Flashmaster, 40-63 mesh silica gel, 50% isohexane-EtOAc)

Sources & evidence

ORD record
ord-7820f7c6f37d467ebbe15e363a08468d
Source dataset
uspto-grants-2015_02
Patent number
US08962609B2

Reaction notes

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