Potassium Carbonate → 4-({3-[3-Azabicyclo[3.2.1]oct-8-yl(methyl)amino]propyl}amino)benzonitrile

HRID 411526

반응식

HRID 411526 반응식
C([N:8]1[CH2:14][CH:13]2[CH:15]([NH:16][CH3:17])[CH:10]([CH2:11][CH2:12]2)[CH2:9]1)C1C=CC=CC=1.CC1C=CC(S(O[CH2:29][CH2:30][CH2:31][NH:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][CH:34]=2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:13]12[CH:15]([N:16]([CH3:17])[CH2:29][CH2:30][CH2:31][NH:32][C:33]3[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][CH:34]=3)[CH:10]([CH2:11][CH2:12]1)[CH2:9][NH:8][CH2:14]2

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 185410303-benzyl-N-methyl-3-azabicyclo[3.2.1]octan-8-amineHCID 218676523-(4-Cyanoanilino)propyl 4-methylbenzenesulfonate

생성물 1

HCID 185409074-({3-[3-Azabicyclo[3.2.1]oct-8-yl(methyl)amino]propyl}amino)benzonitrile수율 65.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

A mixture of 3-benzyl-N-methyl-3-azabicyclo[3.2.1]octan-8-amine (Preparation B; 4.0 g, 17.4 mmol), 3-(4-cyanoanilino)propyl 4-methyl-benzenesulfonate (Preparation G(ii); 5.74 g, 17.4 mmol), and potassium carbonate (2.40 g, 17.4 mmol) in DMF (85 mL) was heated at 90° C. under nitrogen overnight. The mixture was partitioned with water (200 mL) and diethyl ether (150 mL). The aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine (2×30 mL), dried (Na2SO4), filtered and then concentrated in vacuo. The residue was chromatographed on silica gel, eluting with dichloromethane:methanol (98:2), to afford 3.40 g (50%) of the sub-title compound as a white solid.

후처리

  1. customThe mixture was partitioned with water (200 mL) and diethyl ether (150 mL)
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  3. washThe combined organic extracts were washed with brine (2×30 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel
  8. washeluting with dichloromethane:methanol (98:2)

출처 및 근거

ORD 기록
ord-159d2fdcc8c34753ace01f967dbd9955
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559162B2

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