Piperazine → HCID 67829624、化合物

HRID 1494398ノート

反応式

HRID 1494398 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[CH2:8][C:7](=O)[CH2:6][CH2:5]2.[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>C1(C)C=CC=CC=1>[ClH:1].[ClH:1].[N:14]1([CH:7]2[CH2:6][CH2:5][C:4]3[C:9](=[CH:10][C:11]([Cl:12])=[C:2]([Cl:1])[CH:3]=3)[CH2:8]2)[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1

参加物

4

反応物 2

HCID 4837PiperazineHCID 44528536,7-Dichloro-2-tetralone

生成物 1

HCID 67829624HCID 67829624、化合物収率 46.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture consisting of 6,7-dichloro-2-tetralone (4.30 g), piperazine (3.44 g), and 4A molecular sieves (4 g) 100 ml of toluene was stirred overnight under nitrogen and warmed briefly. The sieves were filtered off, and the filtrate was freed of solvent on an evaporator. Seventy-five ml of THF and 6 ml of methanol were added to the residue. The solution was cooled in an ice bath under nitrogen, and 1.24 g of sodium cyanoborohydride was added. Small amounts of gaseous HCl were added periodically until the solution remained acidic. The solution was stirred overnight at ambient temperature, the solvents were evaporated, and the residue was dissolved in dilute HCl. The acidic solution was extracted with three portions of ether and then made basic with sodium hydroxide. The oil which separated was extracted with ether, and the ether solution was dried (Na2SO4). The after evaporation of the ether was dissolved in ethanol, and excess anhydrous HCl was added. The crystalline solid isolated from the ethanol melted at about 272°-275° C. After recrystallization from ethanol there was obtained 1.1 g of the title compound. m.p. 278°-282° C.

後処理

  1. temperaturewarmed briefly
  2. filtrationThe sieves were filtered off
  3. customthe filtrate was freed of solvent on an evaporator
  4. additionSeventy-five ml of THF and 6 ml of methanol were added to the residue
  5. temperatureThe solution was cooled in an ice bath under nitrogen
  6. addition1.24 g of sodium cyanoborohydride was added
  7. additionSmall amounts of gaseous HCl were added periodically until the solution
  8. stirringThe solution was stirred overnight at ambient temperature
  9. customthe solvents were evaporated
  10. dissolutionthe residue was dissolved in dilute HCl
  11. extractionThe acidic solution was extracted with three portions of ether
  12. customThe oil which separated
  13. extractionwas extracted with ether
  14. dry with materialthe ether solution was dried (Na2SO4)
  15. customThe after evaporation of the ether
  16. dissolutionwas dissolved in ethanol
  17. additionexcess anhydrous HCl was added
  18. customThe crystalline solid isolated from the ethanol melted at about 272°-275° C
  19. customAfter recrystallization from ethanol

出典と根拠

ORDレコード
ord-4774b420b9c64f2dbc934c32f3c8478a
出典データセット
uspto-grants-1991_06
特許番号
US05026707

反応ノート

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