Water → (R)-[1-(4-chlorophenyl)-ethyl]-[1-phenyl-ethylidene]-amine

HRID 1003759Notes

Reaction equation

HRID 1003759 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=O)[CH3:12].O>C1(C)C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([N:10]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:12])[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 7410AcetophenoneHCID 1715226(1R)-1-(4-chlorophenyl)ethan-1-amine

Product 1

HCID 54063039(R)-[1-(4-chlorophenyl)-ethyl]-[1-phenyl-ethylidene]-amineYield 47.2%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 1140TolueneSolvent

Procedure

0.3 g of zinc chloride is added to a solution of 20 g (0.128 mol) of (R)-1-(4-chlorophenyl)-ethylamine (97% ee) and 15.6 g (0.13 mol) of acetophenone in 70 ml of toluene at room temperature with stirring, and the mixture is then refluxed for 74 hours at the water separator. The reaction mixture is then filtered. The filtrate is evaporated under reduced pressure to give 15.56 g (47% of theory) of (R)-[1-(4-chlorophenyl)-ethyl]-[1-phenyl-ethylidene]-amine.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. customThe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-84ae4a0a34b4417287adae9bfaa6ce5d
Source dataset
uspto-grants-2000_04
Patent number
US06046351

Reaction notes

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