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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2289882Generated: October 30, 2026

2,3-Dichloro-alpha-methylbenzylamine → HCID 53748281, compound

https://huagongshe.com/reaction/2289882

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2,3-Dichloro-alpha-methylbenzylamineHCID 1215—
ReactantSodium HydroxideHCID 14798—
Reactant(S)-mandelic acidHCID 439616—
Solventtert-Butyl methyl etherHCID 15413—
ProductHCID 53748281HCID 5374828140%

Reaction Conditions

Temperature45 °C

Reaction Steps

A solution consisting of 10 g of (RS)-1-(2,3-dichlorophenyl)ethylamine and 30 g of methyl t-butyl ether was heated to 45° C. while stirring, and a mixture of 3.6 g of L-mandelic acid and 30 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 20 g of methyl t-butyl ether and dried to obtain 7.2 g of diastereomer salt. 21 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 4 g of (R)-1-(2,3-dichlorophenyl)ethylamine. This had the optical purity of 90.4%ee.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06093851
Source datasetuspto-grants-2000_07
ORD IDord-9b0158ab76ec4acea682a8927e4f0df2
Source noteuspto-grants-2000_07