1-Bromo-3-chloropropane → 1-(3-Chloropropyl)pyrrolidin-2-one

HRID 2287633Notes

Reaction equation

HRID 2287633 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].[NH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]1=[O:13].Br[CH2:15][CH2:16][CH2:17][Cl:18].CC(C)([O-])C.[K+].[Na].[K]>C1(C)C=CC=CC=1.C1(C)C(C)=CC=CC=1.C1C=CC=CC=1>[Cl:18][CH2:17][CH2:16][CH2:15][N:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].[Cl:18][CH2:17][CH2:16][CH2:15][N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]1=[O:13]

Participants

11

Reactant 6

HCID 80061-Bromo-3-chloropropaneHCID 120252-PyrrolidoneHCID 126652-PiperidoneHCID 5360545SodiumHCID 5462222PotassiumHCID 23665647Potassium tert-butoxide

Product 2

HCID 111056621-(3-Chloropropyl)pyrrolidin-2-oneHCID 14526712HCID 14526712, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 1140TolueneSolventHCID 7237O-XyleneSolvent

Procedure

In the first method the 2-pyrrolidone (2, n=1) or 2-piperidone (2, n=2) is condensed with 1-bromo-3-chloropropane in the presence of bases selected from potassium tert. butoxide, pulverized alkali metals selected from sodium or potassium in nonpolar solvents selected from benzene, xylene, toluene at a temperature ranging from 110 to 150° C. for 1.15 to 14 hrs to give 1-chloro-3-[2-oxo-pyrrolidin-1-yl]propane (3, n=1) or 1-chloro-3-[2-oxopiperidin-1-yl]propane (3, n=2) which on condensation with appropriately substituted piperazines, gave the required compounds of formula 1. This reaction may be carried out in solvents selected from acetone, methylethyl ketone, tetrahydrofuran or dimethylformamide using bases selected from triethylamine, pyridine, sodium or potassium carbonate and catalysts selected from sodium/potassium iodide to improve the yield of the compound of formula 1.

Sources & evidence

ORD record
ord-abd65f5403fc46358f71006d4adca722
Source dataset
uspto-grants-2000_07
Patent number
US06084097

Reaction notes

Loading…