Triethylamine → HCID 54564163, compound

To a stirred slurry of 1.0 g (5.2 mmole) of the (S)(+)-3-(3-methoxyphenyl)piperidine from Preparation 7, Part B, and 1 ml (7.8 mmole) of triethylamine in 10 ml of toluene, at 0° C., was added, dropwise, a solution of 1.3 g (7.8 mmole) of 3-phenylpropionyl chloride in 5 ml of toluene. The reaction mixture was then allowed to warm to room temperature and stirring was continued for 30 minutes. The reaction mixture was then filtered, and the filtrate was evaporated in vacuo to give a yellow oil. The yellow oil was dissolved in 15 ml of tetrahydrofuran and the resulting solution was added dropwise to a slurry of 910 mg (24 mmole) of lithium aluminum hydride in 15 ml of tetrahydrofuran. The resulting mixture was heated under reflux for 2 hours and then it was cooled in an ice-bath. To the cooled mixture was added, dropwise, with stirring, 5 ml of 3% sodium hydroxide, followed by 20 ml of diethyl ether. Stirring was continued for 15 minutes, and then the mixture was filtered. The filtrate was evaporated in vacuo. The residue was dissolved in toluene and evaporated in vacuo several times. This afforded 1.8 g of material.

1. additionat 0° C., was added
2. filtrationThe reaction mixture was then filtered
3. customthe filtrate was evaporated in vacuo
4. customto give a yellow oil
5. temperatureThe resulting mixture was heated
6. temperatureunder reflux for 2 hours
7. temperatureit was cooled in an ice-bath
8. additionTo the cooled mixture was added
9. stirringdropwise, with stirring
10. stirringStirring
11. waitwas continued for 15 minutes
12. filtrationthe mixture was filtered
13. customThe filtrate was evaporated in vacuo
14. dissolutionThe residue was dissolved in toluene
15. customevaporated in vacuo several times

ORD record

ord-4c48c1aa48554f3e8dbbf13e5d9aaf0e

Source dataset

uspto-grants-1986_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04593037