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

HRID 736467ノート

反応式

HRID 736467 の反応式
[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]

参加物

6

反応物 3

HCID 7841Allyl bromideHCID 8082PiperidineHCID 11430Potassium Carbonate

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8bea15022e914245830c4f119915f816
出典データセット
uspto-grants-2009_09
特許番号
US07595344B2

反応ノート

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