3,3,3-trifluoro-1-phenylpropan-1-amine synthesis

Yield:-

Reaction Conditions:

Stage #1: 4,4,4-trifluoro-2-phenylbutanoic acidwith chloroformic acid ethyl ester;triethylamine in acetone at 0; for 2 h;
Stage #2: with sodium azide in water;acetone; for 3 h;
Stage #3: with hydrogenchloride;sodium hydroxidemore than 3 stages;

Steps:

94.A

Example 94Preparation of Compound 518Step A - synthesis of compound 94B A solution of compound 94 A (3.7Og 17mmol) and Et₃N (2.84mL) in acetone (4OmL) at0 ⁰C was treated with EtOCOCl (1.82mL). After 2 h, NaN₃ (1.88g, 29mmol) in water (2OmL) was added dropwise. After 3 h, the reaction was partitioned between ether and water. The ether phase was dried, filtered and concentrated in vacuo to provide an oil, which was diluted with toluene (2OmL) and heated at 80 ⁰C for 18 h. Cone. HCl (2OmL) was added and the mixture stirred 18h. The reaction mixture was then partitioned between ether and water.Basification of the aqueous with NaOH, extraction with ether, drying and concentration gave compound 94B as a yellow oil.

References:

WO2008/130581,2008,A1 Location in patent:Page/Page column 212