Potassium Hydroxide → 1-[2-Chloro-3-(2,2-dimethylpropoxy)propyl]pyrrolidine

Dry hydrogen chloride gas was bubbled into an ice-cooled solution of 107.7 g (0.5 mole) of α-[(2,2-dimethylpropoxy)methyl]-1-pyrrolidineethanol (the product of Example 3a) in 110 ml of dry toluene until 20.05 g (0.55 mole) was taken up. This solution was added to a stirred ice-cooled suspension of 109.4 g (0.525 mole) of phosphorous pentachloride in 60ml of dry toluene (argon atmosphere) at a rate to keep the reaction temperature between 10°-15° C. After the addition was complete, the ice bath was removed and the reaction mixture was stirred for 1.5 hr. The reaction mixture was added to a stirred ice-cooled solution of 385 ml (4.5 mole) of 45% potassium hydroxide and 700 ml of ice at a rate to keep the reaction temperature between 25°-35° C. The reaction mixture was stirred for 0.5 hr then extracted with toluene. An immiscible oil formed between the layers. The oil was partitioned between dichloromethane and water. The dichloromethane layer and the toluene layer above were combined, dried and concentrated to dryness to give 84.3 g of oil. The oil was distilled (65°-86° C. at 0.35 mm) to give 76.63 g of oily product.

1. customDry hydrogen chloride gas was bubbled into an ice-
2. temperaturecooled
3. custombetween 10°-15° C
4. additionAfter the addition
5. customthe ice bath was removed
6. additionThe reaction mixture was added to a stirred ice-
7. custombetween 25°-35° C
8. stirringThe reaction mixture was stirred for 0.5 hr
9. extractionthen extracted with toluene
10. customAn immiscible oil formed between the layers
11. customThe oil was partitioned between dichloromethane and water
12. customdried
13. concentrationconcentrated to dryness

ORD record

ord-5e9dc3466a4643bbbd107b29fdd519fb

Source dataset

uspto-grants-1989_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04888335