Diisopropylethylamine → N-[(1-(2-Methanesulphonamidoethyl)-4-piperidyl)methyl] 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxamide

HRID 1458606

반응식

HRID 1458606 반응식
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9]([C:11]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]3[CH2:20][CH2:21][CH2:22][O:23][C:12]=23)=[O:10])[CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.Br[CH2:34][CH2:35][NH:36][S:37]([CH3:40])(=[O:39])=[O:38]>C(#N)C.C(Cl)(Cl)Cl>[CH3:40][S:37]([NH:36][CH2:35][CH2:34][N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9]([C:11]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]3[CH2:20][CH2:21][CH2:22][O:23][C:12]=23)=[O:10])[CH2:3][CH2:2]1)(=[O:39])=[O:38]

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 285330N-(2-bromoethyl)methanesulfonamideHCID 9839803N-(4-Piperidylmethyl) 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxamide

생성물 1

HCID 19599423N-[(1-(2-Methanesulphonamidoethyl)-4-piperidyl)methyl] 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxamide수율 11.2%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6342Acetonitrile용매

실험 절차

A stirred solution of N-(4-piperidylmethyl) 3,4-dihydro-2 H-[1,3]oxazino[3,2-a]indole-10-carboxamide (E21, 220 mg, 0.70 mmole) in acetonitrile (8 ml) was treated with diisopropylethylamine (0.24 ml, 1.4 mmole) and N-(2-bromoethyl)methanesulphonamide (D14, 160 mg, 0.77 mmole) and the mixture heated under reflux for 2.5 h. The reaction mixture was concentrated in vacuo and the residue chromatographed on silica gel eluting with dichloromethane/methanol/0.88 ammonia solution (200:10:1). The colourless oil obtained was dissolved in chloroform (30 ml) and washed with water (2×20 ml), then dried (Na2SO4) and concentrated in vacuo. The residue was passed through a short plug of basic alumina eluting with ethyl acetate to afford the title compound as a colourless oil (34 mg, 11%). This was converted to its oxalate salt and crystallised from acetone to give a white solid mp 80°-85° C.

후처리

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 2.5 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue chromatographed on silica gel eluting with dichloromethane/methanol/0.88 ammonia solution (200:10:1)
  5. customThe colourless oil obtained
  6. washwashed with water (2×20 ml)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c32a9de2e34d4e20a79825049211bbc6
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05852014

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