P-Chloroacetophenone → HCID 54063040, compound

HRID 989461Notes

Reaction equation

HRID 989461 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1)=O.[C:11]1([C@@H:17]([NH2:19])[CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>[Cl-].[Zn+2].[Cl-].C1(C)C=CC=CC=1>[C:11]1([C:17](=[N:19][C@H:2]([C:4]2[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=2)[CH3:1])[CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 7467P-ChloroacetophenoneHCID 758181-Phenethylamine, (-)-

Product 1

HCID 54063040HCID 54063040, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 1140TolueneSolvent

Procedure

At first, zinc chloride (0.16 g, 1.1 mmol) was added to a toluene solution (100 ml) containing 16.6 g (107 mmol) of 4-chloroacetophenone (1b) as a ketone and 14.3 g (118 mmol) of (S)-1-phenylethylamine ((S)-2a) as an optically active primary amine. Then, the same steps as those of Example 1-7a were conducted, thereby obtaining 27.3 g of (S)-N-(1-phenylethylidene)-1-(4-chlorophenyl)-ethylamine ((S)-3ba, purity: 95%, yield: 94%).

Sources & evidence

ORD record
ord-7c87065b2e0349ac9bf8072c5cc98d4d
Source dataset
uspto-grants-2003_10
Patent number
US06639100B2

Reaction notes

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