Triethylamine → Methyl 3-(4-oxopiperidin-1-yl)propanoate

HRID 379092ノート

反応式

HRID 379092 の反応式
O.Cl.[O:3]=[C:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.Br[CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14].C([O-])([O-])=O.[K+].[K+].CCN(CC)CC>CC(C)=O>[O:3]=[C:4]1[CH2:9][CH2:8][N:7]([CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH2:6][CH2:5]1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 76934Methyl 3-bromopropanoateHCID 2723901Piperonylamine

生成物 1

HCID 18187970Methyl 3-(4-oxopiperidin-1-yl)propanoate収率 42%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a suspension of 4-oxopiperidine hydrochloride monohydrate (10.0 g, 65.1 mmol) and methyl 3-bromopropanoate (7.8 ml, 71.6 mmol) in acetone (100 ml) was added K2CO3 (9.9 g, 71.6 mmol) and Et3N (9.1 ml, 65.3 mmol). The mixture was refluxed for 24 hours. The solid was removed by filtration and the solvent was evaporated. The residue was partitioned between EtOAc and H2O. The organic extracts were combined and dried over Na2SO4. The solvent was evaporated to give the title compound (15.0 g, 27.0 mmol, 42%) as an oil. 1H NMR (300 MHz, CDCI) δ 3.70 (s, 3H), 2.75-2.85 (mult, 6H), 2.52-2.57 (mult, 2H), 2.42-2.46 (mult, 4H).

後処理

  1. temperatureThe mixture was refluxed for 24 hours
  2. customThe solid was removed by filtration
  3. customthe solvent was evaporated
  4. customThe residue was partitioned between EtOAc and H2O
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated

出典と根拠

ORDレコード
ord-bae778c2af4040f99eed4339b68dca3e
出典データセット
uspto-grants-2001_10
特許番号
US06297260B1

反応ノート

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