Tert-Butylamine → N-tert-Butyl-3-chloropropan-1-amine

A round-bottom, 250 milliliter, three-necked flask was equipped with a magnetic stir bar, 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 15.74 grams, (0.10 moles, 1 equivalent). t-Butylamine 29.26 grams, (0.40 moles, 4 equivalents) was added dropwise via the addition funnel over a period of one hour. 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-chloropropane 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 and extracted 2×75 milliliters with ethyl ether. The organic layer was then dried with magnesium sulfate, filtered, and concentrated on a rotary evaporator, to afford a colorless, slightly hazy solution with a yield=10.47 g (70%); (GC assay=93%).

1. customA round-bottom, 250 milliliter, three-necked flask was equipped with a magnetic stir bar
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. additionAfter addition
6. customsamples of the reaction mixture were removed periodically
7. washwashed with saturated sodium bicarbonate solution
8. customwas consumed
9. additionNext, 75 milliliters of saturated sodium bicarbonate solution and 25 milliliters of distilled water were added to the reaction flask
10. customThe reaction mixture was then transferred to a separatory funnel
11. extractionextracted 2×75 milliliters with ethyl ether
12. dry with materialThe organic layer was then dried with magnesium sulfate
13. filtrationfiltered
14. concentrationconcentrated on a rotary evaporator
15. customto afford a colorless, slightly hazy solution with a yield=10.47 g (70%)

ORD record

ord-58a660ec589c40c8bf282a7d642d2d03

Source dataset

uspto-grants-2002_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06482944B2