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

HRID 1248145노트

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HRID 1248145 반응식
[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

참가 물질

6

반응물 4

HCID 78401-BromopropaneHCID 5462224MagnesiumHCID 212948301-(3-Chloro-5-methylphenyl)-1-cyclobutanecarbonitrileHCID 178455851HCID 178455851, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

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온도
50 °C

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-70c06149320242169d141ae7bf792bb2
출처 데이터셋
uspto-grants-1985_06
특허 번호
US04522828

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