Ethyl Acetate → 2-(4-Benzyl-piperazin-1-yl)-N-methyl-acetamide

HRID 1972726

반응식

HRID 1972726 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:15][C:16]([NH:18][CH3:19])=[O:17].C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:15][C:16]([NH:18][CH3:19])=[O:17])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 667732-chloro-N-methylacetamideHCID 759941-Benzylpiperazine

생성물 1

HCID 368452302-(4-Benzyl-piperazin-1-yl)-N-methyl-acetamide수율 83%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

A mixture of 1-benzyl-piperazine (1.0 g, 5.67 mmol), 2-chloro-N-methylacetamide (671.2 mg, 6.24 mmol, 1.1 eq.), and potassium carbonate (941 mg, 6.81 mmol, 1.2 eq.) in anhydrous THF (23 mL) was stirred at 60° C. under N2 for 18 h. The mixture was cooled to rt and poured into EtOAc. The organic phase was washed with water and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by MPLC (Biotage®, gradient elution 1:4:5 v/v MeOH:Acetone:DCM) to give 1.16 g (83%) of the product as a white solid. 1H-NMR (300 MHz, DMSO-d6) 7.62 to 7.56 (broad d, 1H), 7.33 to 7.20 (m, 5H), 3.45 (s, 2H), 2.85 (s, 2H), 2.58 (d, 3H), 2.44 to 2.33 (broad s, 8H); ES-MS m/z 248.2 [M+H]+, RT (min) 0.33.

후처리

  1. temperatureThe mixture was cooled to rt
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by MPLC (Biotage®, gradient elution 1:4:5 v/v MeOH:Acetone:DCM)

출처 및 근거

ORD 기록
ord-3cf0cccfa4de48788a451027f19e9182
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431695B2

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