2-Bromopropane → HCID 16243895, compound

Participants

Reaction Steps

A solution of 1,2,3,4-tetrahydro-3-isoquinoline-carboxylic acid (9 g, 42 mmol), 2-bromopropane (8 ml, 84 mmol) and 1N NaOH (168 mmol) in ethanol (170 ml) was refluxed for 5 hours, then 2-bromopropane (8 ml, 84 mmol) and 1N NaOH (168 ml, 168 mmol) were added and the mixture was refluxed for 5 hours. Ethanol was removed and the aqueous solution was treated with 6N hydrochloric acid to pH=7. Unreacted starting material was recovered by filtration and the solvent was removed under reduced pressure. The crude was dissolved in ethanol, the inorganics salts were filtered off and the organic solution was evaporated under reduced pressure. This procedure was repeated three times yielding 8.1 g (yield 87%) of pure N-isopropyl-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid which was used for the next step without further purification.

Provenance & Evidence