1-Bromopropane → 1-[1-(3-Chloro-5-methylphenyl)cyclobutyl]butylamine hydrochloride

HRID 35711ノート

反応式

HRID 35711 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:13]#[N:14])[CH2:12][CH2:11][CH2:10]2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH2:15]([Mg]Br)[CH2:16][CH3:17].BrCCC.[Mg]>CCOCC>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH:13]([NH2:14])[CH2:15][CH2:16][CH3:17])[CH2:12][CH2:11][CH2:10]2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

参加物

6

反応物 4

HCID 78401-BromopropaneHCID 5462224MagnesiumHCID 212948301-(3-Chloro-5-methylphenyl)-1-cyclobutanecarbonitrileHCID 178455851HCID 178455851、化合物

生成物 1

HCID 130833061-[1-(3-Chloro-5-methylphenyl)cyclobutyl]butylamine hydrochloride

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
50 °C

実験手順

A solution of 1-(3-chloro-5-methylphenyl)-1-cyclobutanecarbonitrile (8.0 g) in ether (40 ml) was added to a solution of propyl magnesium bromide [prepared by the reaction of 1-bromopropane (6.7 g) and magnesium (1.3 g)] in ether (80 ml) and the mixture heated under reflux for two and a half hours. Two thirds of the ether was evaporated off and then, after cooling, a solution of sodium borohydride (3.5 g) in ethanol (150 ml) added. The mixture was maintained at 50° C. for one hour and water (50 ml) and then 5N hydrochloric acid (50 ml) added. The ether layer was separated, dried and evaporated to yield a solid which was recrystallised from propan-2-ol to give 1-[1-(3-chloro-5-methylphenyl)cyclobutyl]butylamine hydrochloride (m.p. 145°-146° C.).

後処理

  1. temperaturethe mixture heated
  2. temperatureunder reflux for two and a half hours
  3. customTwo thirds of the ether was evaporated off
  4. temperatureafter cooling
  5. additiona solution of sodium borohydride (3.5 g) in ethanol (150 ml) added
  6. additionwater (50 ml) and then 5N hydrochloric acid (50 ml) added
  7. customThe ether layer was separated
  8. customdried
  9. customevaporated
  10. customto yield a solid which
  11. customwas recrystallised from propan-2-ol

出典と根拠

ORDレコード
ord-5ee67020d89b43c1a014d0cbd69883d4
出典データセット
uspto-grants-1988_08
特許番号
US04767790

反応ノート

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