Sodium Hydroxide → (R)-1-(3,4-dichlorophenyl)ethanamine

Temperature

45 °C

A solution consisting of 41 g of (RS)-1-(3,4-dichlorophenyl)ethylamine and 78 g of methyl t-butyl ether was heated to 45° C. while stirring, and a mixture of 14.6 g of L-mandelic acid and 90 g of methyl t-butyl ether was added thereto over about 30 minutes, followed by stirring at the same temperature for 30 minutes. Then, after cooled to 20° C. over 6 hours, the precipitated crystals were filtered, washed twice with 40 g of methyl t-butyl ether and dried to obtain 32.9 g of diastereomer salt. 82 g of a 5% aqueous sodium hydroxide solution was added to the crystals, followed by extraction twice with 10 g of methyl t-butyl ether. The solvent was distilled off from the resulting organic layer to obtain 18.2 g of (R)-1-(3,4-dichlorophenyl)ethylamine. This had the optical purity of 87.4%ee.

1. additionwas added
2. stirringby stirring at the same temperature for 30 minutes
3. temperatureThen, after cooled to 20° C. over 6 hours
4. filtrationthe precipitated crystals were filtered
5. washwashed twice with 40 g of methyl t-butyl ether
6. customdried
7. customto obtain 32.9 g of diastereomer salt
8. extractionfollowed by extraction twice with 10 g of methyl t-butyl ether
9. distillationThe solvent was distilled off from the resulting organic layer

ORD record

ord-5e99564cfad84e268d9a7d29d9c18dde

Source dataset

uspto-grants-1998_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05739401