Thionyl Chloride → HCID 131712024, compound

2-(1-Benzylpiperidin-4-oxy)acetic acid, hydrochloride, (7.0 g) and thionyl chloride (5 ml) in dry chloroform (100 ml) were heated under reflux for 21/2 hours. The solvent was evaporated in vacuo and the resulting acid chloride taken up in chloroform (50 ml) and added dropwise to a solution of n-butylamine (5 ml) in chloroform (50 ml) with stirring at 0°. The solution was stirred at 0° for 4 hours then left at room temperature overnight. The chloroform solution was washed with water (3×50 ml), sodium hydroxide solution (3×50 ml, 2 N) and hydrochloric acid solution (3×50 ml, 2 N). The aqueous acid solution was basified to pH 12 and extracted with chloroform (3×100 ml). The chloroform extract was dried and the solvent evaporated in vacuo. The residue in ether was treated with ethereal hydrogen chloride, the resulting solid collected, washed with ether and dried to give N-n-butyl-2-(1-benzylpiperidin-4-oxy)acetamide, hydrochloride (3.5 g) identified by n.m.r. spectroscopy.

1. temperatureunder reflux for 21/2 hours
2. customThe solvent was evaporated in vacuo
3. additionadded dropwise to a solution of n-butylamine (5 ml) in chloroform (50 ml)
4. stirringThe solution was stirred at 0° for 4 hours
5. washThe chloroform solution was washed with water (3×50 ml), sodium hydroxide solution (3×50 ml, 2 N) and hydrochloric acid solution (3×50 ml, 2 N)
6. extractionextracted with chloroform (3×100 ml)
7. extractionThe chloroform extract
8. customwas dried
9. customthe solvent evaporated in vacuo
10. additionThe residue in ether was treated with ethereal hydrogen chloride
11. customthe resulting solid collected
12. washwashed with ether
13. customdried

ORD record

ord-604985e41022481b855141dd151ecd3a

Source dataset

uspto-grants-1981_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04243666