Pyrrolidine → 4-Chloro-1-(pyrrolidin-1-yl)butan-1-one

HRID 1110378Notes

Reaction equation

HRID 1110378 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:6][CH2:7][CH2:8][CH2:9][C:10](Cl)=[O:11]>O>[Cl:6][CH2:7][CH2:8][CH2:9][C:10]([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:11]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 783704-Chlorobutyryl chloride

Product 1

HCID 3040794-Chloro-1-(pyrrolidin-1-yl)butan-1-oneYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred and cooled (ice bath) solution of 71.12 parts of pyrrolidine in 210 parts of petroleumether were added dropwise 70.5 parts of 4-chlorobutanoyl chloride at a temperature below 15° C. Upon completion, stirring was continued overnight at room temperature. Water was added. The product was extracted with dichloromethane. The extract was separated, dried, filtered and evaporated. The residue was distilled at 266 Pa bp. 137° C., yielding 45 parts (51%) of 1-(4-chloro-1-oxobutyl)pyrrolidine (int. 1).

Workup

  1. stirringUpon completion, stirring
  2. extractionThe product was extracted with dichloromethane
  3. customThe extract was separated
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. distillationThe residue was distilled at 266 Pa bp. 137° C.

Sources & evidence

ORD record
ord-6fbefa2758264ec99994ef8fda1b46ac
Source dataset
uspto-grants-1990_12
Patent number
US04975439

Reaction notes

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