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Sodium Cyanide → 2-{1-Azabicyclo[2.2.2]octan-4-yl}acetonitrile

HRID 1923408
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HRID 1923408 반응식
[N:1]12[CH2:8][CH2:7][C:4]([CH2:9]O)([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.S([O-])(=O)(=O)C.CS(Cl)(=O)=O.[C-:21]#[N:22].[Na+]>C(Cl)(Cl)Cl.CN(C)C=O.C(N(CC)CC)C>[N:1]12[CH2:8][CH2:7][C:4]([CH2:9][C:21]#[N:22])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2
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참가 물질

8

반응물 4

HCID 8929Sodium CyanideHCID 31297Methanesulfonyl chlorideHCID 85257Methanesulfonate2회HCID 1413111-Azabicyclo(2.2.2)octane-4-methanol

생성물 1

HCID 220566352-{1-Azabicyclo[2.2.2]octan-4-yl}acetonitrile수율 72%

시약·촉매·용매 3

HCID 6212
Chloroform
용매
HCID 6228Dimethylformamide용매
HCID 8471Triethylamine용매

실험 절차

Quinuclidin-4-ylmethanol (1.94 g, 0.014 moles) was converted to the corresponding mesylate by treatment with methane sulphonyl chloride and triethylamine in chloroform. The mesylate was dissolved in dimethylformamide (50 ml) and treated with sodium cyanide (1.4 g, 0.028 moles) at 120° C. for 18 hours. The mixture was cooled and concentrated in vacuo. The residue was partitioned between saturated potassium carbonate and chloroform. The organic layer was separated and dried (Na2SO4), filtered and evaporated to dryness. Chromatography on silica gel eluting with 0-10% methanol/chloroform gave the title compound 1.5 g (72%). M.S. (+ve electrospray) m/z 151 (MH+, 100%).

후처리

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between saturated potassium carbonate and chloroform
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated to dryness

출처 및 근거

ORD 기록
ord-f9fa8c0d47a04ce6aec068dc333378d9
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
USRE043390E1

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