2-(3-(3,4-Dichlorophenyl)-4-aminobutyl)oxytetrahydropyran → 4-Amino-3-(3,4-dichlorophenyl)-1-butanol

To a mechanically stirred solution of 2-(3,4-dichlorophenyl)-4-(tetrahydropyran-2-yloxy)butylamine (550 g) in methanol (3300 mL) was added in one portion 6.0N hydrochloric acid (352 mL), resulting in a slight exotherm. After being stirred for 3 hours, the reaction mixture was evaporated, and the residue was diluted with water to 3 L volume. This solution was extracted with ether (2 times 500 mL), basified with sodium hydroxide pellets (100 g), and extracted with ethyl acetate (4 times 500 mL). The combined ethyl acetate extracts were washed (800 mL saturated sodium chloride), dried, and evaporated to give the alcohol as an amber oil (367 g) that solidified under high vacuum; NMR: 7.39 (d, 1, J=8.2), 7.28 (d, 1, J=2.0), 7.04 (dd, 1, J=8.2, 2.0), 3.65 (m, 1), 3.50 (m, 1), 2.90 (m, 2), 2.71 (m, 1), 2.25 (m, 2), 1.86 (m, 2).

1. customresulting in a slight exotherm
2. customthe reaction mixture was evaporated
3. additionthe residue was diluted with water to 3 L volume
4. extractionThis solution was extracted with ether (2 times 500 mL)
5. extractionextracted with ethyl acetate (4 times 500 mL)
6. washThe combined ethyl acetate extracts were washed (800 mL saturated sodium chloride)
7. customdried
8. customevaporated

ORD record

ord-1e40766456d04c17b34dcc341d95a371

Source dataset

uspto-grants-1997_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05654299