1-(4-Chlorophenyl)ethylamine → HCID 86749736, compound

HRID 1078414Notes

Reaction equation

HRID 1078414 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.[C:11]([OH:20])(=[O:19])[C@@H:12]([C@H:14]([C:16]([OH:18])=[O:17])[OH:15])[OH:13]>>[C:16]([CH:14]([CH:12]([C:11]([OH:20])=[O:19])[OH:13])[OH:15])([OH:18])=[O:17].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 978031-(4-Chlorophenyl)ethylamineHCID 444305L-Tartaric acid

Product 1

HCID 86749736HCID 86749736, compound

Procedure

The (-)-enantiomer (starting material for Example 57) was prepared in conventional manner as follows. A warm solution of (±)1-(4-chlorophenyl)ethylamine (101 g) and L(+)tartaric acid (97.3 g) in IMS (7 l) was allowed to cool slowly and to stand at ambient temperature for 3 days. The solid formed was collected by filtration, washed with IMS and recrystallised twice from IMS to give (-)1-(4-chlorophenyl)ethylamine (+) tartrate, m.p. 195°-196° C. The salt was suspended in water and basified with aqueous ammonia (specific gravity 0.88). The mixture was extracted with diethyl ether to give (-) 1-(4-chlorophenyl)ethylamine (free base) which was distilled at 122°-124° C. (28 mmHg). Chiral HPLC indicated enantiomeric purity of 96.8%.

Workup

  1. customThe (-)-enantiomer (starting material for Example 57) was prepared in conventional manner
  2. temperatureto cool slowly
  3. customThe solid formed
  4. filtrationwas collected by filtration
  5. washwashed with IMS
  6. customrecrystallised twice from IMS

Sources & evidence

ORD record
ord-18723eb16cb84f57b1eb1a596a9f739e
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

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