1,4-Dichlorobutane → HCID 12855246, compound

Sodium hydride (3.87 g of 50% dispersion in oil, 0.0807 mole) was suspended and stirred in 80 ml of dry dimethylformamide. A solution of 1,4-dichlorobutane (44 ml, 0.404 mole) and 2-piperidone (8 g, 0.0807 mole) in 100 ml of dimethylformamide was added dropwise over 1 hour, maintaining the temperature at 25°-30° C. by use of a water bath. The reaction mixture was stirred for 16 hours at room temperature, then byproduct salt removed by filtration and the mother liquor evaporated in vacuo to one-tenth volume. The resulting concentrate was distributed between 100 ml of water and 100 ml of hexane. The lower, oily phase of three phases was separated, diluted with 50 ml of methylene chloride, dried over magnesium sulfate, filtered and evaporated to yield 1-(4-chloro-1-butyl)-2-piperidone as an oil [14.3 g; pnmr(CDCl3) delta 1.4-1.83 (4H, m), 3.03-3.72 (6H, m), 4.10-4.43 (2H, t, J=7)].

1. temperaturemaintaining the temperature at 25°-30° C. by use of a water bath
2. custombyproduct salt removed by filtration
3. customthe mother liquor evaporated in vacuo to one-tenth volume
4. concentrationThe resulting concentrate
5. customThe lower, oily phase of three phases was separated
6. additiondiluted with 50 ml of methylene chloride
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. customevaporated

ORD record

ord-7a65351ba4bc4cbeb67e6a94ac266793

Source dataset

uspto-grants-1982_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04337250