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ChemicalBook CAS DataBase List 1-[1,1'-Biphenyl]-4-ylethenyl Ester 1-Piperidinecarboxylic Acid
1186236-75-8

1-[1,1'-Biphenyl]-4-ylethenyl Ester 1-Piperidinecarboxylic Acid synthesis

1synthesis methods
-

Yield:1186236-75-8 26%

Reaction Conditions:

Stage #1: biphenyl-4-acetaldehydewith sodium hydride in dimethyl sulfoxide;oil;
Stage #2: piperidine carbamoyl chloride in dimethyl sulfoxide;oil; for 3 h;

Steps:

9

Example 9 Piperidine-1-carboxylic acid l-biphenyl-4-yl- vinyl ester (ST 4070) A solution of NaH (60% in oil, 56 mg, 14 mmol) in 3 ml of dry DMSO was stirred for 2 h at 50°C and allowed to return to room temperature. (Biphenyl-3-yl)ethanone (2.5 g, 13 mmol) in 1.5 ml of DMSO was added dropwise and the resulting solution was stirred for 1 h prior to addition of piperidine-1-carbonyl chloride (2.07 g, 14 mmol) in 0.5 ml of DMSO. The reaction mixture was stirred for 3 h. The latter was diluted by addition of AcOEt and washed with water. After removal of the solvent under vacuo and purification through flash chromatography (hexaneiClHbCb = 1:1), piperidine-1-carboxylic acid l-biphenyl-4-yl- vinyl ester was obtained (1 g, 26%).1H NMR CDCl3 δ: 1.50-1.75 (m, 6H); 3.45-3.50 (m, 2H); 3.57-3.66 (m, 2H); 5.04 (d, IH, J = 1.84 Hz); 5.46 (d, IH, J = 1.84 Hz); 7.27-7.78 (m, 9H).

References:

WO2009/109504,2009,A1 Location in patent:Page/Page column 23-24

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