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

HRID 1003758

Reaction equation

HRID 1003758 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.[CH3:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=O.O>C1(C)C=CC=CC=1.CCCCO.CCCCO.CCCCO.CCCCO.[Ti]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([N:10]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH3:11])[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 7467P-ChloroacetophenoneHCID 1715226(1R)-1-(4-chlorophenyl)ethan-1-amine

Product 1

HCID 54223262(R)-[1-(4-chlorophenyl)-ethyl]-[1-(4-chlorophenyl)-ethylidene]-amineYield 66%

Reagents, catalysts & solvents 2

HCID 521701TetrabutoxytitaniumCatalyst3×HCID 1140TolueneSolvent

Procedure

3 g of tetrabutyl ortho-titanate are added to a solution of 52 g (0.35 mol) of (R)-1-(4-chlorophenyl)-ethylamine (97% ee) and 51.7 g (0.353 mol) of 4-chloroacetophenone in 300 ml of toluene at room temperature with stirring, and then the mixture is refluxed for 2 hours at the water separator. A further 2 g of tetrabutyl ortho-titanate are added, and the mixture is refluxed for a further 6 hours. A further 2 g of tetrabutyl ortho-titanate are then added, and the mixture is then refluxed for 3 hours. The reaction mixture is then filtered. The filtrate is evaporated under reduced pressure to give 67.3 g (66% of theory) of (R)-[1-(4-chlorophenyl)-ethyl]-[1-(4-chlorophenyl)-ethylidene]-amine.

Workup

  1. temperaturethe mixture is refluxed for a further 6 hours
  2. temperaturethe mixture is then refluxed for 3 hours
  3. filtrationThe reaction mixture is then filtered
  4. customThe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-175fb17104e34e0ea98fcc3135e30c45
Source dataset
uspto-grants-2000_04
Patent number
US06046351

Linked notes

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