Water → 2-[(Ethyl-pyridin-4-ylmethyl-amino)-methyl]-1-aza-bicyclo[2.2.2]octan-3-one

HRID 2356375

반응식

HRID 2356375 반응식
Cl.[CH2:2]=[C:3]1[C:8](=[O:9])[CH:7]2[CH2:10][CH2:11][N:4]1[CH2:5][CH2:6]2.O.C([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:3]([N:4]([CH2:2][CH:3]1[C:8](=[O:9])[CH:7]2[CH2:10][CH2:11][N:4]1[CH2:5][CH2:6]2)[CH2:5][C:6]1[CH:17]=[CH:16][N:15]=[CH:18][CH:19]=1)[CH3:2]

참가 물질

5

반응물 3

HCID 962WaterHCID 8471TriethylamineHCID 184012841-Azabicyclo(2.2.2)octan-3-one, 2-methylene-, hydrochloride (1:1)

생성물 1

HCID 588995622-[(Ethyl-pyridin-4-ylmethyl-amino)-methyl]-1-aza-bicyclo[2.2.2]octan-3-one

시약·촉매·용매 1

HCID 74236Tetrabutylammonium Bromide촉매

반응 조건

온도
80 °C

실험 절차

To a stirred solution of 2-methylene-3-quinuclidinone hydrochloride (0.5 g, 0.0036 mol) in water (3 ml) N-(4-pyridylmethyl)ethylamine (0.49 g, 0.0036 mol), triethylamine (1.09 g, 0.0108 mol) and tetra-n-butyl ammonium bromide (116 mg, 0.00036 mol) were added and the reaction mixture were allowed to stir at 80° C. for 18 h. The completion of reaction was monitored by tlc. The reaction mixture was quenched with ice-cold water (10 ml), extracted with dichloromethane (2×50 ml), organic layers were washed with 10% NaHCO3 solution, brine and dried over sodium sulphate, filtered and concentrated to get the crude product which was purified as yellow solids (200 mg, 22%) by flash column chromatography on neutral silica gel using chloroform as eluent.

후처리

  1. customThe completion of reaction
  2. customThe reaction mixture was quenched with ice-cold water (10 ml)
  3. extractionextracted with dichloromethane (2×50 ml), organic layers
  4. washwere washed with 10% NaHCO3 solution, brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e5a1120a58cc4d9687d2bd7ad3177757
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07759361B2

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