N,N'-Dimethylethylenediamine → 1-(3-(Benzylthio)-2-methylphenyl)pyrrolidin-2-one

HRID 389678Notes

Reaction equation

[CH2:1]([S:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](Br)[C:10]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:17]1[CH2:21][CH2:20][CH2:19][C:18]1=[O:22].CNCCNC.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I>[CH2:1]([S:8][C:9]1[C:10]([CH3:16])=[C:11]([N:17]2[CH2:21][CH2:20][CH2:19][C:18]2=[O:22])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Intermediate 83 (7 g, 23.87 mmol), pyrrolidin-2-one (4.06 g, 47.74 mmol), CuI (909 mg, 4.77 mmol), N,N′-dimethylethylene diamine (10.28 ml, 95.49 mmol) and K2CO3 (7.25 g, 52.52 mmol) were suspended in toluene (10 ml) under N2 and heated to 110° C. for 16 h. After cooling to RT the reaction mixture was quenched by the addition of 100 ml water and extracted with ethyl acetate (three times). The organic layers were combined and washed with water and sat. aq NaCl-solution, dried with Na2SO4, filtered and evaporated to dryness, and purified by silica gel chromatography.

Workup

temperatureAfter cooling to RT the reaction mixture
customwas quenched by the addition of 100 ml water
extractionextracted with ethyl acetate (three times)
washwashed with water and sat. aq NaCl-solution
dry with materialdried with Na2SO4
filtrationfiltered
customevaporated to dryness
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-9d5ab9fcdb5542cba0f96af3891d264f
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08378092B2

Reaction notes

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