Hydrochloric Acid → (R)-1-(3-Methoxyphenyl)ethylamine

HRID 374331Notes

Reaction equation

HRID 374331 reaction equation
CC1(C)C[C@@H]1C(O)=O.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:17]([NH3+:19])[CH3:18])[CH:14]=[CH:15][CH:16]=1.Cl.[OH-].[Na+]>CCCCCC>[CH3:9][O:10][C:11]1[CH:12]=[C:13]([C@H:17]([NH2:19])[CH3:18])[CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10192561(1S)-2,2-Dimethylcyclopropane-1-carboxylic acidHCID 19809737HCID 19809737, compound

Product 1

HCID 7020759(R)-1-(3-Methoxyphenyl)ethylamineYield 100%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

The aqueous phases from Example 2 (87.4 g) and Example 3 (854.4 g), after decomposition of the 1-(3-methoxyphenyl)ethylammonium salts with hydrochloric acid and extraction with hexane, were combined and mixed with 94 g of 25 percent sodium hydroxide solution. The pure amine was extracted three times with 100 ml each of dichloromethane. After distilling off the solvent and vacuum distillation of the residue, 62.1 g of (R)-(+)-1-(3-methoxyphenyl)-ethylamine [content (GC) : 100%, [α]D20 : 22.0° (c=10, methanol)] was obtained as a colorless liquid.

Workup

  1. extractionThe pure amine was extracted three times with 100 ml each of dichloromethane
  2. distillationAfter distilling off
  3. distillationthe solvent and vacuum distillation of the residue

Sources & evidence

ORD record
ord-1993df2099204f90a54081f010ba6afd
Source dataset
uspto-grants-1992_11
Patent number
US05166417

Reaction notes

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