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

HRID 974965ノート

反応式

HRID 974965 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e25de71c0b26490493a691aea975216d
出典データセット
uspto-grants-1997_03
特許番号
US05607950

反応ノート

読み込み中…