Dimethylformamide → Ethyl 1-(4-methoxybenzyl)piperidine-3-carboxylate

HRID 228492ノート

反応式

HRID 228492 の反応式
[NH:1]1[CH2:11][CH2:10][CH2:9][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:2]1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C.[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Cl)=[CH:27][CH:26]=1>C(OCC)(=O)C>[CH2:7]([O:6][C:4]([CH:3]1[CH2:9][CH2:10][CH2:11][N:1]([CH2:29][C:28]2[CH:31]=[CH:32][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)[CH2:2]1)=[O:5])[CH3:8]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 98969Ethyl nipecotate

生成物 1

HCID 3160450Ethyl 1-(4-methoxybenzyl)piperidine-3-carboxylate収率 82.8%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Combine Ethyl nipecotate (9.9 mL, 63.6 mmol), K2CO3 (13.2 g, 95.4 mmol), and DMF (300 mL) at room temperature under a Nitrogen atmosphere. Heat reaction mixture to 70° C. for 30 minutes then add 4-Methoxybenzyl chloride (9.5 mL, 69.9 mmol). Stir the reaction for 5 hours at 70° C. then cool the reaction mixture to room temperature and stir for an additional 12 hours. Add Ethyl acetate to the reaction mixture and extract with water and then brine. Dry the organic layer over Na2SO4. Concentrate under reduced pressure and flash chromatograph using 3:1 Hexanes:Ethyl acetate to give 14.6 g (82% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 1.2 (3H, t), 1.4-1.6 (2H, m), 1.6-1.7 (1H, m), 1.9-2.1 (2H, m), 2.2 (1H, t), 1.5-1.8 (2H, m), 2.9 (1H, d), 3.5 (2H, q), 3.8 (3H, s), 4.1 (2H, dd), 6.8 (2H, d), 7.2 (2H, d); MS m/z 278 (M+1).

後処理

  1. customat room temperature
  2. temperatureHeat
  3. customreaction mixture to 70° C. for 30 minutes
  4. customthe reaction for 5 hours at 70° C.
  5. stirringstir for an additional 12 hours
  6. extractionAdd Ethyl acetate to the reaction mixture and extract with water
  7. dry with materialDry the organic layer over Na2SO4
  8. concentrationConcentrate under reduced pressure and flash chromatograph

出典と根拠

ORDレコード
ord-53741a6a6ced4653ace718304312e7dc
出典データセット
uspto-grants-2009_07
特許番号
US07560463B2

反応ノート

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