Реакция #64654

Уравнение реакции

title compound

phenylmethyl α-methylenebenzenepropanoate

2-dimethylaminoethanethiol hydrochloride

piperidine

benzyltrimethylammonium hydroxide

→

title compound

Выход 24.0%

phenylmethyl α-[[[2-(dimethylamino)ethyl]thio]methyl]benzene-propanoate

Выход 24.0%

Растворители

methanol

MeOH

Условия реакции

Обработка

1. 1
   ДругоеThe solvent was removed on a rotary evaporator
2. 2
   Другоеthe residue was purified by flash chromotography on silica gel
3. 3
   Промывкаeluting with 20:1 CH2Cl2

Методика

The title compound of Step 10 (1.5 g, 5.95 mmol) was dissolved under argon in methanol (22 mL). To this solution was added 2-dimethylaminoethanethiol hydrochloride (843 mg, 5.95 mmol), piperidine (0.78 mL, 7.85 mmol) and benzyltrimethylammonium hydroxide (0.25 mL, 0.6 mmol), and the mixture was stirred at room temperature for 16 hours. The solvent was removed on a rotary evaporator and then the residue was purified by flash chromotography on silica gel, eluting with 20:1 CH2Cl2 :MeOH to give the pure title compound (0.5 g, 24% yield). 1H NMR: 300 MHz spectrum consistent with proposed structure. Anal: calcd. for C21H27NO2S+0.2H2O: C, 69.85; H, 7.65; N, 3.88. Found: C, 69.58; H, 7.60; N, 3.98.

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