Potassium Cyanide → 1-Azabicyclo(2.2.2)octane-3-carbonitrile

HRID 2293433노트

반응식

HRID 2293433 반응식
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C:2]2=O.C(C1C=C(C(C)C)C=C(C(C)C)C=1S(NN)(=O)=O)(C)C.[C-:30]#[N:31].[K+]>CO>[C:30]([CH:3]1[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1)#[N:31]

참가 물질

5

반응물 3

HCID 9032Potassium CyanideHCID 3593332,4,6-TriisopropylbenzenesulphonohydrazideHCID 5661192-Quinuclidone

생성물 1

HCID 1428651-Azabicyclo(2.2.2)octane-3-carbonitrile수율 23.6%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Quinuclidinone (24.2 g, 0.19 mol) and 2,4,6-triisopropylbenzene sulphonohydrazide (72 g, 0.24 mol) (250 ml) were stirred together in anhydrous methanol for 3 hours. Potassium cyanide (33.8 g, 0.51 mol) was added and the mixture heated under reflux for 5 hours. The material isolated, after evaporation of the solvent, was partitioned between water and dichloromethane. The organic phase was dried (sodium sulphate) and evaporated and the residue fractionally distilled under reduced pressure to give 3-cyano-quinuclidine (6.1 g), approximate b.p. 95°-100° at 13 N.m-2 (0.1 mmHg).

후처리

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 5 hours
  3. customThe material isolated
  4. customafter evaporation of the solvent
  5. customwas partitioned between water and dichloromethane
  6. dry with materialThe organic phase was dried (sodium sulphate)
  7. customevaporated
  8. distillationthe residue fractionally distilled under reduced pressure

출처 및 근거

ORD 기록
ord-5335a9bcb1f848ca8d0d18f13ff919c3
출처 데이터셋
uspto-grants-1997_11
특허 번호
US05686463

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