Propylamine → HCID 178456835, compound

1-(4-Chlorophenyl)-1,4-dihydroisoquinol-3-one (6.2 g, 24 mmol) was dissolved in dry methylene chloride (30 ml) and stirred under nitrogen. A solution of triethyloxonium tetrafluoroborate in methylene chloride (1M), (24 ml) was added in one portion at room temperature. After 3 h at room temperature, a solution of n-propylamine (2.0 g, 34 mmol) in ethanol (20 ml) was added and the mixture refluxed for 24 h. The solution was cooled, the solvent removed under reduced pressure and the residue partitioned between ethyl acetate (200 ml) and 10% sodium hydroxide (100 ml). The organic layer was separated, acidified with 5M sulphuric acid (2×50 ml) and washed with water (100 ml). The combined aqueous phases were basified (Care) with 10% sodium hydoxide and the oil so produced extracted with ethyl acetate (2×100 ml). The combined ethyl acetate layers were washed with brine (50 ml) and dried over sodium sulphate. The solution was filtered and reduced to 100 ml under reduced pressure. Ethereal hydrogen chloride was added and the solvent was removed under reduced pressure. Toluene (50 ml) was added to the foam so produced and evaporated off. The foam that remained was dried in the vacuum over (90° C., 1 mm) to give 1-(4-chlorophenyl)-3-n-propylamino-1,4-dihydroisoquinoline hydrochloride (3.1 g, 38%).

1. temperaturethe mixture refluxed for 24 h
2. temperatureThe solution was cooled
3. customthe solvent removed under reduced pressure
4. customthe residue partitioned between ethyl acetate (200 ml) and 10% sodium hydroxide (100 ml)
5. customThe organic layer was separated
6. washwashed with water (100 ml)
7. customthe oil so produced
8. extractionextracted with ethyl acetate (2×100 ml)
9. washThe combined ethyl acetate layers were washed with brine (50 ml)
10. dry with materialdried over sodium sulphate
11. filtrationThe solution was filtered
12. additionEthereal hydrogen chloride was added
13. customthe solvent was removed under reduced pressure
14. additionToluene (50 ml) was added to the foam
15. customso produced
16. customevaporated off
17. customThe foam that remained was dried in the vacuum over (90° C., 1 mm)

ORD record

ord-d851fa4786054d5bb41ff2fb37042554

Source dataset

uspto-grants-1986_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04578393