1,2,3,4-Tetrahydroisoquinoline → 3,4-Dihydroisoquinoline

HRID 398325

反応式

HRID 398325 の反応式
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.C1C(=O)N(Br)C(=O)C1.[OH-].[Na+]>C(Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]=1

参加物

5

反応物 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 14798Sodium HydroxideHCID 67184N-bromobutanimide

生成物 1

HCID 767053,4-Dihydroisoquinoline

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

9.4 ml of 1,2,3,4-tetrahydroisoquinoline are dissolved in 200 ml of DCM and 14.7 g of NBS are gradually added. The mixture is left stirring at RT, cooling slightly in order to maintain a temperature of less than 40° C. for 30 minutes, after which 50 ml of 10N NaOH are added and the mixture is left stirring for 1 hour at RT. The organic phase is separated out after settling of the phases has taken place and is washed with 100 ml of water and then twice with 100 ml of 4N HCl. The aqueous phases are washed with DCM and then brought to pH=9 by addition of concentrated NH4OH. This mixture is extracted with DCM, dried over Na2SO4 and evaporated to dryness. The oil obtained is distilled off. 7.16 g of the expected compound are obtained, b.p.=50-54° C. at 0.05 mbar.

後処理

  1. waitThe mixture is left
  2. temperaturecooling slightly in order
  3. temperatureto maintain a temperature of less than 40° C. for 30 minutes
  4. waitthe mixture is left
  5. stirringstirring for 1 hour at RT
  6. customThe organic phase is separated out
  7. washis washed with 100 ml of water
  8. washThe aqueous phases are washed with DCM
  9. additionbrought to pH=9 by addition of concentrated NH4OH
  10. extractionThis mixture is extracted with DCM
  11. dry with materialdried over Na2SO4
  12. customevaporated to dryness
  13. customThe oil obtained
  14. distillationis distilled off

出典と根拠

ORDレコード
ord-17009ae711264a15b780897882dd2b0a
出典データセット
uspto-grants-2003_08
特許番号
US06610882B2

関連ノート

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