Acetic Acid → N-(3-Phenylpropyl)-1-(3-trifluoromethylphenyl)-2-aminopropane Hydrochloride

HRID 1106947

反応式

HRID 1106947 の反応式
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH2:9][C:10](=O)[CH3:11])[CH:6]=[CH:7][CH:8]=1.[C:15]1([CH2:21][CH2:22][CH2:23][NH2:24])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)(=O)C.[BH4-].[Na+].[ClH:31]>CO>[ClH:31].[C:15]1([CH2:21][CH2:22][CH2:23][NH:24][CH:10]([CH3:11])[CH2:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:14])([F:13])[F:1])[CH:4]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

7

反応物 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 162593-PhenylpropylamineHCID 891011-(alpha,alpha,alpha-Trifluoro-m-tolyl)acetoneHCID 4311764Sodium borohydride

生成物 1

HCID 18790270N-(3-Phenylpropyl)-1-(3-trifluoromethylphenyl)-2-aminopropane Hydrochloride収率 37%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 1-(3-trifluoromethylphenyl)-2-propanone (102 mg, 0.50 mmol), 3-phenyl-1-propylamine (86 mg, 0.64 mmol), glacial acetic acid (8 mg, 0.13 mmol), and MeOH (2 mL) was allowed to stir at room temperature for 0.5 h. To this mixture was added over a 4-h period sodium borohydride (19 mg, 0.50 mmol) and the mixture was allowed to stir at room temperature for 20 h. The solvents were removed by warming under reduced pressure to give a small amount of an oil which was cooled and treated with 10% HCl. The crude product separated as a white solid, 122 mg (68%), mp 135-145° C. The crystals were dissolved in H2O and the solution was extracted with Et2O. The H2O portion was separated, the H2O was evaporated, and the crystals reformed; recrystallization from acetone gave 66 mg (37%) of colorless crystals, mp 167-169° C.

後処理

  1. stirringto stir at room temperature for 20 h
  2. customThe solvents were removed
  3. temperatureby warming under reduced pressure
  4. customto give a small amount of an oil which
  5. temperaturewas cooled
  6. customThe crude product separated as a white solid, 122 mg (68%), mp 135-145° C
  7. dissolutionThe crystals were dissolved in H2O
  8. extractionthe solution was extracted with Et2O
  9. customThe H2O portion was separated
  10. customthe H2O was evaporated
  11. customrecrystallization from acetone

出典と根拠

ORDレコード
ord-a7957351e1c1486ca0eebf9f5ac40e98
出典データセット
uspto-grants-2000_05
特許番号
US06057371

関連ノート

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