1-Amino-2-propanol → HCID 17332070、化合物

HRID 839812

反応式

HRID 839812 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:14][C:11]([CH:12]=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[NH2:15][CH2:16][CH:17]([OH:19])[CH3:18].[BH4-].[Na+]>CO>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:14][C:11]([CH2:12][NH:15][CH2:16][CH:17]([OH:19])[CH3:18])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 41-Amino-2-propanolHCID 6761845-(4-Chlorophenyl)-2-furaldehydeHCID 4311764Sodium borohydride

生成物 1

HCID 17332070HCID 17332070、化合物収率 99.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

5-(4-Chlorophenyl)furfural (42 g, 0.20 mole) was added in portions to a solution of 15 g (0.20 mole) of 1-amino-2-propanol in 200 ml of methanol with stirring at room temperature. The mixture was stirred for 0.5 hr., heated under reflux for 1.5 hr., and allowed to stand overnight. To this solution 7.6 g (0.20 mole) of sodium borohydride was added in portions over 1 hr. at 15°-20°. The solution was stirred at ambient temperature for 1 hr. and heated under reflux for 0.5 hr. The solvent was removed on a rotary evaporator, and the residual solid was partitioned between chloroform and water. The layers were separated, and the aqueous layer was extracted once with chloroform. The combined chloroform layers were dried over MgSO4 and concentrated on a rotary evaporator. The residual solid was dissolved in 150 ml of absolute methanol with warming and was treated with 40 ml of methanolic HCl with cooling. Anhydrous ether (1 1.) was added, and the solid which was deposited was collected by filtration to give 30 g (50%) of 1-[5-(4-chlorophenyl)furfurylamino]-2-propanol hydrochloride. One recrystallization from CH3CN gave an analytical sample; m.p. 197°-202°.

後処理

  1. stirringThe mixture was stirred for 0.5 hr
  2. temperature, heated
  3. temperatureunder reflux for 1.5 hr
  4. customat 15°-20°
  5. stirringThe solution was stirred at ambient temperature for 1 hr
  6. temperatureand heated
  7. temperatureunder reflux for 0.5 hr
  8. customThe solvent was removed on a rotary evaporator
  9. customthe residual solid was partitioned between chloroform and water
  10. customThe layers were separated
  11. extractionthe aqueous layer was extracted once with chloroform
  12. dry with materialThe combined chloroform layers were dried over MgSO4
  13. concentrationconcentrated on a rotary evaporator
  14. dissolutionThe residual solid was dissolved in 150 ml of absolute methanol
  15. temperaturewith warming
  16. additionwas treated with 40 ml of methanolic HCl
  17. temperaturewith cooling
  18. additionAnhydrous ether (1 1.) was added
  19. filtrationthe solid which was deposited was collected by filtration

出典と根拠

ORDレコード
ord-a0065273a616495bbb5ac8993c3cbe6f
出典データセット
uspto-grants-1978_06
特許番号
US04097499

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