Cyclopropyl phenyl ketone → cyclopropyl(phenyl)methanamine

HRID 128699

反応式

HRID 128699 の反応式
[C:1]1([C:7]([CH:9]2[CH2:11][CH2:10]2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:18].[Na+]>CO>[CH:9]1([CH:7]([NH2:18])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:11][CH2:10]1

参加物

5

反応物 3

HCID 77029Cyclopropyl phenyl ketoneHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 3281515cyclopropyl(phenyl)methanamine収率 76%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Stir 100 g of cyclopropyl phenyl ketone in 2000 ml of methanol with 500 g of previously dried ammonium acetate and 50 g of sodium cyanoborohydride at 50° C. for 4 days under argon in the presence of 4 Å molecular sieve. After cooling, filter off the molecular sieve and then add concentrated hydrochloric acid to take the pH to 2. Evaporate the solution to dryness under vacuum and take up the residue in water. The aqueous phase is washed with ethyl ether and then alkalinised by adding concentrated potassium hydroxide solution so that the pH is above 10. Extract twice with methylene chloride, wash with saturated sodium chloride solution, dry over anhydrous magnesium sulphate and then concentrate under vacuum to obtain α-cyclopropylbenzylamine, which is used without any further purification in the next step.

後処理

  1. temperatureAfter cooling
  2. filtrationfilter off the molecular sieve
  3. additionadd concentrated hydrochloric acid
  4. customEvaporate the solution to dryness under vacuum
  5. washThe aqueous phase is washed with ethyl ether
  6. additionby adding concentrated potassium hydroxide solution so that the pH is above 10
  7. extractionExtract twice with methylene chloride
  8. washwash with saturated sodium chloride solution
  9. dry with materialdry over anhydrous magnesium sulphate
  10. concentrationconcentrate under vacuum

出典と根拠

ORDレコード
ord-45da5684a33e4f85a30f9695f5ecacac
出典データセット
uspto-grants-1995_11
特許番号
US05464847

関連ノート

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