Acetic Acid → 1-Benzyl-4-phenyl-1,2,3,6-tetrahydropyridine

HRID 276902노트

반응식

HRID 276902 반응식
[C:1]1([C:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O)(=O)C.C(OCC)(=O)C>ClC(Cl)C>[CH2:13]([N:10]1[CH2:9][CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 8857Ethyl AcetateHCID 825531,2,3,6-Tetrahydro-4-phenylpyridine

생성물 1

HCID 5636091-Benzyl-4-phenyl-1,2,3,6-tetrahydropyridine수율 50%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

1,2,3,6-Tetrahydro-4-phenylpyridine (410 mg, 2.6 mmol), benzaldehyde (300 mg, 2.9 mmol), sodium triacetoxyborate (1.1 g, 5.2 mmol) and acetic acid (1.5 ml, 26 mmol) were stirred in dichloroethane at a room temperature for 14 hours. To the reaction solution was added ethyl acetate, and the resulting solution was washed with sodium hydroxide aqueous solution (1 N) and saturated brine and dried with anhydrous sodium sulfate. Then the solvent was evaporated under a reduced pressure. Thereafter, the resulting residue was separated and purified by a silica gel column chromatography to obtain 330 mg of the title compound (1.3 mmol, 45% in yield).

후처리

  1. washthe resulting solution was washed with sodium hydroxide aqueous solution (1 N) and saturated brine
  2. dry with materialdried with anhydrous sodium sulfate
  3. customThen the solvent was evaporated under a reduced pressure
  4. customThereafter, the resulting residue was separated
  5. custompurified by a silica gel column chromatography

출처 및 근거

ORD 기록
ord-d9ca1c3daf274125b95fbf68b4162893
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355642B1

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