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

HRID 2293433ノート

反応式

HRID 2293433 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 1428651-Azabicyclo(2.2.2)octane-3-carbonitrile収率 23.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5335a9bcb1f848ca8d0d18f13ff919c3
出典データセット
uspto-grants-1997_11
特許番号
US05686463

反応ノート

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