Benzyl Bromide → HCID 21462995、化合物

HRID 1940558ノート

反応式

HRID 1940558 の反応式
[CH2:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)[CH3:2].[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[BH4-].[Na+]>CN(C)C=O.C(O)C>[CH2:9]([N:6]1[CH2:7][CH:8]=[C:3]([CH2:1][CH3:2])[CH2:4][CH2:5]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

6

反応物 3

HCID 7498Benzyl BromideHCID 108224-EthylpyridineHCID 4311764Sodium borohydride

生成物 1

HCID 21462995HCID 21462995、化合物収率 34.1%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 4-ethylpyridine (3.0 g, 28 mmol) in anhydrous dimethylformamide (10 ml) was treated with benzyl bromide (3.7 ml, 31 mmol) and the mixture was stirred at room temperature for two hours. The reaction mixture was diluted with absolute ethanol (60 ml), treated with sodium borohydride (1.3 g, 35 mmol) and stirred at reflux for one hour. The solvent was evaporated in vacuo and the residue partitioned between dichloromethane and water. The organic phase was separated, dried (MgSO4) and evaporated in vacuo. The residue was chromatographed with 1:1 hexane/ethyl acetate as eluant to give the title compound (1.92 g, 34% over two steps) as a colourless oil; δH (CDCl3) 1.00 (3H, t, J 7.5 Hz, CH2CH3), 1.94-2.12 (4H, m, CH2CH3 and tetrahydropyridinyl CH2), 2.55 (2H, t, J 6.3 Hz, tetrahydropyridinyl CH2), 2.90-3.00 (2H, m, tetrahydropyridinyl CH2), 3.58 (2H, s, PhCH2N), 5.32-5.40 (1H, m, tetrahydropyridinyl 5-H), and 7.20-7.40 (5H, m, ArH); m/z (CI+, NH3) 202 (M+1)+.

後処理

  1. stirringstirred
  2. temperatureat reflux for one hour
  3. customThe solvent was evaporated in vacuo
  4. customthe residue partitioned between dichloromethane and water
  5. customThe organic phase was separated
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customThe residue was chromatographed with 1:1 hexane/ethyl acetate as eluant

出典と根拠

ORDレコード
ord-90ed90dd3f11426d87ec7938429d06db
出典データセット
uspto-grants-1997_12
特許番号
US05700809

反応ノート

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