Chloroacetyl chloride → HCID 579939, compound

A solution of 1,2,5,6-tetrahydropyridine (41.5 grams; 0.5 mol) and triethylamine (50 grams) in benzene (1 l.) was placed into a 2 l. glass reaction flask equipped with a mechanical stirrer, reflux condenser and addition funnel. Chloroacetyl chloride (56.5 grams; 0.5 mol) was slowly added, with stirring, over a period of about 15 minutes. After the addition was completed stirring was continued for an additional period of about 15 minutes. After this time the reaction mixture was cooled and filtered to remove the triethylamine hydrochloride which had formed. The remaining benzene solution was stripped of solvent to yield a dark colored oil. The oil was then distilled under reduced pressure, to yield 1-(α-chloroacetyl)-1,2,5,6-tetrahydropyridine as a pale yellow oil having a boiling point of 88° to 91° C. at 0.35 mm Hg. pressure, an index of refraction of 1.5224 at 25° C. and having the following elemental analysis as calculated for C7H10ClNO.

1. customglass reaction flask
2. customequipped with a mechanical stirrer
3. temperaturereflux
4. additioncondenser and addition funnel
5. additionAfter the addition
6. stirringwas completed stirring
7. waitwas continued for an additional period of about 15 minutes
8. temperatureAfter this time the reaction mixture was cooled
9. filtrationfiltered
10. customto remove the triethylamine hydrochloride which
11. customhad formed
12. customto yield a dark colored oil
13. distillationThe oil was then distilled under reduced pressure

ORD record

ord-88a76edacb2d44bf821aa248a8a4d66f

Source dataset

uspto-grants-1976_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03998808