2-Pyrrolidone → 1-(3-Morpholino-5-nitrophenyl)pyrrolidin-2-one

HRID 1431771Notes

Reaction equation

HRID 1431771 reaction equation
Cl[C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[NH:25]1[CH2:29][CH2:28][CH2:27][C:26]1=[O:30]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)(C)(C)C>[O:14]1[CH2:15][CH2:16][N:11]([C:4]2[CH:3]=[C:2]([N:25]3[CH2:29][CH2:28][CH2:27][C:26]3=[O:30])[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=2)[CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 120252-PyrrolidoneHCID 62657Potassium Phosphate, TribasicHCID 596310694-(3-Chloro-5-nitrophenyl)morpholine

Product 1

HCID 596311461-(3-Morpholino-5-nitrophenyl)pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6386tert-ButanolSolvent

Procedure

Prepared according to Procedure W using palladium (II) acetate (4.63 mg, 0.021 mmol), tetramethyl t-butyl XPhos (0.030 g, 0.062 mmol), 4-(3-chloro-5-nitrophenyl)morpholine (0.100 g, 0.412 mmol), tripotassium phosphate (0.122 g, 0.577 mmol), 2-pyrrolidinone (0.044 mL, 0.577 mmol), and tert-butanol (1 mL). Purification by column chromatography (silica; 0-50% EtOAc in hexanes) afforded 1-(3-morpholino-5-nitrophenyl)pyrrolidin-2-one as an orange amorphous solid. Mass Spectrum (ESI) m/e=292.2 (M+1).

Workup

  1. customPrepared
  2. customPurification by column chromatography (silica; 0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-bb9e426389ad463f87c74344a23e40ac
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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