1-PHENYLPIPERIDINE-4-CARBALDEHYDE synthesis
- Product Name:1-PHENYLPIPERIDINE-4-CARBALDEHYDE
- CAS Number:111153-74-3
- Molecular formula:C12H15NO
- Molecular Weight:189.25
697306-45-9
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Yield:111153-74-3 90%
Reaction Conditions:
with N-(tert-butyl)benzenesulfinimidoyl chloride;1,8-diazabicyclo[5.4.0]undec-7-ene in dichloromethane at -78 - -60; for 1 h;
Steps:
295 Reference Example 295; 1-phenylpiperidine-4-carbaldehyde
(1-PHENYL-PIPERIDIN-4-YL)-METHANOL (0.81 g, 4.23 mmol) and DBU (1.29 g, 8.46 mmol) were dissolved in dehydrating dichloromethane (17 mL) and the mixture was cooled TO-78°C. Thereto was added a solution of N-tert- butylphenylsulfinimidoyl chloride (1.0 g/) in dichloromethane (5 mL) and the mixture was stirred while MAINTAINING-60°C or below for 1 hr. Water was added to the reaction solution and the mixture was extracted with diethyl ether. The extract was dried (MGSO4) and concentrated. The residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate = 4/1) to give the title compound (720 mg, yield 90%). 1H NMR (400 MHz, CDC13) 8 ppm: 1.75-1. 85 (m, 2 H), 2.00- 2.06 (m, 2 H), 2.36-2. 46 (m, 1 H), 2.83-2. 90 (m, 2 H), 3.61 (t, J = 3.8 Hz, 1 H), 3.64 (t, J = 3.8 Hz, 1 H), 6.84- 6.96 (m, 3 H), 7.23-7. 29 (m, 2 H), 9.71 (s, 1 H).
References:
WO2004/46107,2004,A1 Location in patent:Page 227-228
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