Sodium Iodide → 2-(3-Cyano-3,3-diphenylpropyl)-1-(3,4-methylenedioxyphenethyl)piperidine

HRID 974965노트

반응식

HRID 974965 반응식
[C:1]([C:3]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][NH:7]1)#[N:2].[CH2:24]1[O:35][C:34]2[CH:33]=[CH:32][C:28]([CH2:29][CH2:30]Br)=[CH:27][C:26]=2[O:25]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C.C(OCC)(=O)C.O>[C:1]([C:3]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][N:7]1[CH2:30][CH2:29][C:28]1[CH:32]=[CH:33][C:34]2[O:35][CH2:24][O:25][C:26]=2[CH:27]=1)#[N:2]

참가 물질

8

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 122072243,4-Methylenedioxyphenethyl bromideHCID 199701912-(3-Cyano-3,3-diphenylpropyl)piperidine

생성물 1

HCID 199701872-(3-Cyano-3,3-diphenylpropyl)-1-(3,4-methylenedioxyphenethyl)piperidine수율 9.3%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 2-(3-cyano-3,3-diphenylpropyl)piperidine (217 mg, 0.74 mmol--see Preparation 18), 3,4-methylenedioxyphenethyl bromide (186 mg, 0.82 mmol--see Preparation 12), potassium carbonate (1.0 g) and sodium iodide (20 mg) in acetonitrile (10 ml) was heated under reflux for 48 hours, allowed to cool to room temperature and diluted with ethyl acetate and water. The organic layer was dried over sodium sulphate and evaporated. The residue was purified by chromatography on silica using dichloromethane plus 0-5% methanol as eluant. Appropriate fractions were combined and evaporated to give the title compound (31 mg, 9%) as a colourless oil, which was characterised as containing 0.75 of an equivalent of water.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 48 hours
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. customevaporated
  5. customThe residue was purified by chromatography on silica
  6. customevaporated

출처 및 근거

ORD 기록
ord-e25de71c0b26490493a691aea975216d
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05607950

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