Sodium Iodide → HCID 19772580、化合物

HRID 344684ノート

反応式

HRID 344684 の反応式
[CH3:1][O:2][C:3]([C:5]1([N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12](=[O:15])[CH2:13][CH3:14])[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)=[O:4].Br[CH2:23][CH2:24][OH:25].C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(#N)C>[OH:25][CH2:24][CH2:23][N:8]1[CH2:9][CH2:10][C:5]([C:3]([O:2][CH3:1])=[O:4])([N:11]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:12](=[O:15])[CH2:13][CH3:14])[CH2:6][CH2:7]1

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 108982-BromoethanolHCID 2724431Norcarfentanil

生成物 1

HCID 19772580HCID 19772580、化合物収率 96.9%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 4-methoxycarbonyl-4-(N'-phenylpropionamido)piperidine (7.34 g, 25 mmol), 2-bromoethanol (3.96 g, 32 mmol), sodium carbonate (20.0 g, 189 mmol), and sodium iodide (1.0 g) in acetonitrile (200ml) was heated to reflux for three days. The reaction mixture was cooled and filtered. The filtrate was concentrated under vacuum yielding an oily residue. The residue was chromatographed on silica gel (250 g; ethyl acetate/hexane; 1:4) to yield 1-(2-hydroxyethyl)-4-methoxycarbonyl-4-(N'-phenylpropionamido)piperidine (8.1 g, 96%) as an oil.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for three days
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under vacuum
  6. customyielding an oily residue
  7. customThe residue was chromatographed on silica gel (250 g; ethyl acetate/hexane; 1:4)

出典と根拠

ORDレコード
ord-0a1d0857030e4e41999a13bd5ef55443
出典データセット
uspto-grants-1991_10
特許番号
US05053411

反応ノート

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