Hydrochloric Acid → N-[2-(2-methoxyphenyl)ethyl]heptan-1-amine

HRID 2112041

反応式

HRID 2112041 の反応式
[CH2:1]([NH:8][C:9](=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].B.CSC.Cl>C1COCC1>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH2:10][CH2:9][NH:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 3375995HCID 3375995、化合物HCID 12423031(Dimethyl sulfide)trihydroboron

生成物 1

HCID 68868898N-[2-(2-methoxyphenyl)ethyl]heptan-1-amine収率 54.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

N-Heptyl-2-(2-methoxyphenyl)acetamide (2.00 g, 7.594 mmol) was dissolved in THF (10 ml) and was cooled to zero degrees under argon atmosphere. (Methylthio)methane compound with borane (1:1) (1.442 g, 18.984 mmol) was added and the mixture was refluxed for 5 hours. After the mixture was cooled to room temperature, 5 ml HCl (10%) was gently added and the mixture was stirred overnight. The solvent was removed by evaporation. EtOAc (20 ml) was added and the organic phase was washed with K2CO3 (2M, 2×20 ml). The crude was purified by flash cromatography (started with isocratic heptane/EtOAc 50/50 and then the EtOAc concentration was increased to 100%, (silica gel 60 0.004-0.063 mm). The product containing fractions were pooled and the EtOAc was removed by evaporation to give 1.037 g of N-[2-(2-methoxyphenyl)ethyl]heptan-1-amine (yield 54.8%).

後処理

  1. temperaturewas cooled to zero degrees under argon atmosphere
  2. temperaturethe mixture was refluxed for 5 hours
  3. customThe solvent was removed by evaporation
  4. additionEtOAc (20 ml) was added
  5. washthe organic phase was washed with K2CO3 (2M, 2×20 ml)
  6. customThe crude was purified by flash cromatography (
  7. concentrationthe EtOAc concentration
  8. temperaturewas increased to 100%, (silica gel 60 0.004-0.063 mm)
  9. additionThe product containing fractions
  10. customthe EtOAc was removed by evaporation

出典と根拠

ORDレコード
ord-c81f42268c274e64ba5c70a232e01d16
出典データセット
uspto-grants-2009_04
特許番号
US07521461B2

関連ノート

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