Chloroacetyl chloride → HCID 21490114, compound

HRID 1973628Notes

Reaction equation

HRID 1973628 reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][CH:4]([CH3:7])[NH:3]1.C(N(CC)CC)C.[Cl:15][CH2:16][C:17](Cl)=[O:18]>C1C=CC=CC=1>[Cl:15][CH2:16][C:17]([N:3]1[CH:4]([CH3:7])[CH2:5][CH2:6][CH:2]1[CH3:1])=[O:18]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 960342,5-Dimethylpyrrolidine

Product 1

HCID 21490114HCID 21490114, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 2,5-dimethylpyrrolidine (15 grams; 0.15 mol) and triethylamine (15 grams) in benzene (150 ml) was charged into a 250 ml glass reaction flask equipped with stirrer, reflux condenser and addition funnel. Chloroacetyl chloride (18 grams; 0.15 mol) was then slowly added, with vigorous stirring, over a period of several minutes. After the addition was completed stirring was continued for about 15 minutes. After this time the reaction mixture was filtered to remove the triethylamine hydrochloride which had formed. The filtered reaction mixture was then stripped of benzene under reduced pressure to yield a dark colored oil. The oil was distilled under vacuum to yield 1-(α-chloroacetyl)-2,5-dimethylpyrrolidine as a colorless oil having a boiling point of 89° to 90° C. at 0.1 mm of mercury pressure, and a refractive index at 25° C. of 1.4863.

Workup

  1. customequipped with stirrer
  2. temperaturereflux
  3. additioncondenser and addition funnel
  4. additionAfter the addition
  5. filtrationAfter this time the reaction mixture was filtered
  6. customto remove the triethylamine hydrochloride which
  7. customhad formed
  8. customThe filtered reaction mixture
  9. customto yield a dark colored oil
  10. distillationThe oil was distilled under vacuum

Sources & evidence

ORD record
ord-9eebbdcd08df433eb453aa31aaf5ec11
Source dataset
uspto-grants-1976_12
Patent number
US03998808

Reaction notes

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