Reaction #2200609

Reaction equation

Sodium hydroxide

Pyrrolidine

chloroacetyl chloride

chloroacetyl chloride

→

N-(chloroacetyl)pyrrolidine

Yield 48.6%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   Temperaturedropwise maintaining the internal temperature below 15° C
2. 2
   workup.STIRRINGwith vigorous stirring such that the inside temperature
3. 3
   Otherdid not exceed 20° C
4. 4
   workup.STIRRINGThe mixture was stirred for 15 minutes
5. 5
   Otherthe aqueous layer was separated
6. 6
   WashThe organic layer was washed with saturated sodium bicarbonate solution (2×200 mL), water (1×200 mL)
7. 7
   Dryingdried over anhydrous sodium sulfate
8. 8
   OtherThe solvent was removed in vacuo
9. 9
   Otherthe residue was recrystallized from hexane
10. 10
    Otherto give 64.5 g (48.6% yield) of white plate crystals

Procedure

Pyrrolidine (63.9 g, 0.9 mole) was taken up in CH2Cl2 (640 mL) and cooled to 0° C. in a salt-ice water bath. To the stirred mixture was added chloroacetyl chloride (101.8 g in 450 mL of CH2Cl2, 0.9 mole) dropwise maintaining the internal temperature below 15° C. After adding the chloroacetyl chloride, the mixture was stirred for one hour at 5° C. Sodium hydroxide solution (7 M, 190 mL) was added with vigorous stirring such that the inside temperature did not exceed 20° C. The mixture was stirred for 15 minutes and the aqueous layer was separated. The organic layer was washed with saturated sodium bicarbonate solution (2×200 mL), water (1×200 mL) and dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was recrystallized from hexane to give 64.5 g (48.6% yield) of white plate crystals; mp 43° C.

Source