Hydrochloric Acid → HCID 13455624、化合物

HRID 1032510ノート

反応式

HRID 1032510 の反応式
[CH2:1]([N:4]([CH2:23][CH2:24][CH3:25])[C:5](=O)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:9]([NH2:21])[CH:8]=1)[CH2:2][CH3:3].B.[ClH:27].O>O1CCCC1>[ClH:27].[ClH:27].[CH2:14]([O:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][N:4]([CH2:1][CH2:2][CH3:3])[CH2:23][CH2:24][CH3:25])=[CH:8][C:9]=1[NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6331BoraneHCID 136292992-(3-Amino-4-benzyloxyphenyl)acetic acid dipropylamide

生成物 1

HCID 13455624HCID 13455624、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 13.9 g of 2-(3-amino-4-benzyloxyphenyl)acetic acid dipropylamide in 65 ml of tetrahydrofuran is added dropwise under a nitrogen atmosphere into 12 ml of a one-molar solution of borane in tetrahydrofuran, cooled to +5° C., during a period of 20 minutes. Subsequently, the mixture is agitated for 4 hours at room temperature and refluxed for 22 hours. The mixture is combined with semiconcentrated hydrochloric acid and water and the tetrahydrofuran is distilled off. The aqueous solution is then adjusted to a pH value of 10 with sodium hydroxide and extracted by shaking with ether. The ether solution yields, after evaporation and chromatography on silica gel with methylene chloride/acetone (1:1), 8.93 g of pure 2-benzyloxy-5-(2-dipropylaminoethyl)-aniline as an oil. Treatment of this product with 2N HCl in methanol and evaporation yield 2-benzyloxy-5-(2-dipropylaminoethyl)aniline, dihydrochloride, mp 111°-112° C.

後処理

  1. temperaturecooled to +5° C., during a period of 20 minutes
  2. temperaturerefluxed for 22 hours
  3. distillationthe tetrahydrofuran is distilled off
  4. extractionextracted
  5. stirringby shaking with ether
  6. customThe ether solution yields
  7. customafter evaporation and chromatography on silica gel with methylene chloride/acetone (1:1), 8.93 g of pure 2-benzyloxy-5-(2-dipropylaminoethyl)-aniline as an oil
  8. customTreatment of this product with 2N HCl in methanol and evaporation

出典と根拠

ORDレコード
ord-0c3b4cb8fbb34904b8702341f04874d5
出典データセット
uspto-grants-1990_09
特許番号
US04958026

反応ノート

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