Hydrochloric Acid → N-[2-(4-chlorophenyl)ethyl]-N-heptylamine

HRID 2112062ノート

反応式

HRID 2112062 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=O)=[CH:4][CH:3]=1.B.CSC.Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 36599732-(4-chlorophenyl)-N-heptylacetamideHCID 12423031(Dimethyl sulfide)trihydroboron

生成物 1

HCID 43130216N-[2-(4-chlorophenyl)ethyl]-N-heptylamine収率 61.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

2-(4-Chlorophenyl)-N-heptylacetamide (1.045 g, 3.902 mmol) was dissolved in THF (10 ml) and was cooled to 0° C. under argon atmosphere. (Methylthio)methane compound with borane (1:1) (0.741 g, 9.756 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 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 flashcromatography (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 was pooled and the EtOAc was removed by evaporation to give 0.609 g of N-[2-(4-chlorophenyl)ethyl]-N-heptylamine (yield 61.5%).

後処理

  1. temperaturethe mixture was refluxed for 5 hours
  2. temperatureAfter the mixture was cooled to room temperature
  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 flashcromatography (
  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-57e358f6c40144f1aa4d6bd71a750f87
出典データセット
uspto-grants-2009_04
特許番号
US07521461B2

反応ノート

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