Benzyl Bromide → HCID 21462995, 화합물

HRID 1940558노트

반응식

HRID 1940558 반응식
[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

참가 물질

6

반응물 3

HCID 7498Benzyl BromideHCID 108224-EthylpyridineHCID 4311764Sodium borohydride

생성물 1

HCID 21462995HCID 21462995, 화합물수율 34.1%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6228Dimethylformamide용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-90ed90dd3f11426d87ec7938429d06db
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05700809

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