1-Bromo-3-chloropropane → HCID 11608071, compound

A round-bottom, 250 milliliter, three-necked flask was equipped with a mechanical stirrer, a Claisen adapter, equipped with a thermocouple and a dry-ice condenser with a gas inlet, and a pressure-equalizing dropping funnel. This apparatus was baked in an oven overnight at 125° C., assembled hot, and purged with argon until cool. The reaction flask was charged with 1-bromo-3-chloropropane 15.75 grams, (0.10 moles, 1 equivalent) and cyclohexane 8.68 grams, (0.10 moles, 1 equivalent). The reaction mixture was stirred with a magnetic stir bar. 1-Methylhomopiperizine 22.64 grams, (0.20 moles, 2 equivalents) was added dropwise via the addition funnel over a period of thirty-three minutes. A hexane/dry ice cooling bath was applied as needed to maintain a reaction temperature no greater than 35° C. After addition was complete, samples of the reaction mixture were removed periodically, washed with saturated sodium bicarbonate solution, and assayed for unreacted 1-bromo-3-chloropropane by gas chromatography (GLC). The reaction was allowed to stir until 1-bromo-3-chloro-propane was consumed. Next, 75 milliliters of saturated sodium bicarbonate solution and 25 milliliters of distilled water were added to the reaction flask. The reaction mixture was then transferred to a separatory funnel (homogeneous mixture). The mixture was extracted 2×75 milliliters with ethyl ether. The resulting organic layer was then dried with magnesium sulfate, filtered, and concentrated on a rotary evaporator, to afford a slightly hazy solution with a yield=42%; (GC assay=98.3%).

1. customA round-bottom, 250 milliliter, three-necked flask was equipped with a mechanical stirrer
2. customa Claisen adapter, equipped with a thermocouple and a dry-ice condenser with a gas inlet
3. custompurged with argon
4. temperatureuntil cool
5. customA hexane/dry ice cooling bath was applied
6. temperatureto maintain a reaction temperature no greater than 35° C
7. additionAfter addition
8. customsamples of the reaction mixture were removed periodically
9. washwashed with saturated sodium bicarbonate solution
10. stirringto stir until 1-bromo-3-chloro-propane
11. customwas consumed
12. additionNext, 75 milliliters of saturated sodium bicarbonate solution and 25 milliliters of distilled water were added to the reaction flask
13. customThe reaction mixture was then transferred to a separatory funnel
14. extractionThe mixture was extracted 2×75 milliliters with ethyl ether
15. dry with materialThe resulting organic layer was then dried with magnesium sulfate
16. filtrationfiltered
17. concentrationconcentrated on a rotary evaporator
18. customto afford a slightly hazy solution with a yield=42%

ORD record

ord-6545d90961994fdbb22beb8d47ce26c0

Source dataset

uspto-grants-2002_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06482944B2