Carbon Tetrachloride → 1-[(2-chloro-1H-pyrrol-1-yl)methyl]-4-propylpyrrolidin-2-one

HRID 2043699Notes

Reaction equation

HRID 2043699 reaction equation
[CH2:1]([CH:4]1[CH2:8][N:7]([CH2:9][N:10]2[CH:14]=[CH:13][CH:12]=[CH:11]2)[C:6](=[O:15])[CH2:5]1)[CH2:2][CH3:3].[Cl:16]N1C(=O)CCC1=O.C(Cl)(Cl)(Cl)Cl>C1COCC1>[Cl:16][C:14]1[N:10]([CH2:9][N:7]2[CH2:8][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:5][C:6]2=[O:15])[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 31398ChlorosuccinimideHCID 577431024-propyl-1-(1H-pyrrol-1-ylmethyl)pyrrolidin-2-one

Product 1

HCID 577430721-[(2-chloro-1H-pyrrol-1-yl)methyl]-4-propylpyrrolidin-2-oneYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-propyl-1-(1H-pyrrol-1-ylmethyl)pyrrolidin-2-one x264 (0.182 g, 0.88 mmol) is dissolved in absolute THF (3 ml). A solution of N-chlorosuccinimide (0.118 g, 1 eq) in absolute THF (1 ml) is added dropwise in a flow of argon at 0° C. The obtained solution is allowed to heat up slowly to room temperature in the cooling bath under stirring for 16 h. CCl4 (30 ml) is then added to the obtained solution. A small amount of a precipitate is filtered off, and the filtrate is evaporated. 1-[(2-chloro-1H-pyrrol-1-yl)methyl]-4-propylpyrrolidin-2-one 299 is isolated from the residue by reverse-phase HPLC (eluent: acetonitrile/water).

Workup

  1. filtrationA small amount of a precipitate is filtered off
  2. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-794138a0464a455aae3994595c949796
Source dataset
uspto-grants-2013_11
Patent number
US08586623B2

Reaction notes

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