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

HRID 379092노트

반응식

HRID 379092 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-bae778c2af4040f99eed4339b68dca3e
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06297260B1

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