Allyl bromide → 1-(Prop-2-en-1-yl)piperidine

HRID 736467노트

반응식

HRID 736467 반응식
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:7](Br)[CH:8]=[CH2:9].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH2:9]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH:8]=[CH2:7]

참가 물질

6

반응물 3

HCID 7841Allyl bromideHCID 8082PiperidineHCID 11430Potassium Carbonate

생성물 1

HCID 1397561-(Prop-2-en-1-yl)piperidine

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

The piperidine from Example 114 (56 mg, 0.15 mmol) was dissolved in dimethylformamide (2 mL) and was treated with allyl bromide (17 μL, 0.18 mmol), and potassium carbonate (63 mg, 0.45 mmol) and the mixture was stirred at r.t. for 4 hrs. The mixture was diluted with water (2 mL) and the solution was washed with ethyl acetate (3×10 mL). The organic phase was dried (MgSO4) and evaporated to give a pale oil which was purified by column chromatography on silica gel eluting with 80% ethyl acetate in hexanes to give the N-allylpiperidin. 1H NMR (CDCl3) 7.42-7.37 (4H, m), 7.13-7.02 (2H, m), 6.90-6.83 (1H, m), 5.83-5.71 (1H, m), 5.12-5.08 (2H, m), 2.99-2.95 (2H, m), 2.86 (2H, d, J=6.5 Hz), 2.84-2.38 (4H, m), and 1.91-1.85 (2H, m); MS MH+=412(414).

후처리

  1. washthe solution was washed with ethyl acetate (3×10 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated
  4. customto give a pale oil which
  5. customwas purified by column chromatography on silica gel eluting with 80% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-8bea15022e914245830c4f119915f816
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07595344B2

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