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

HRID 1248145Notes

Reaction equation

HRID 1248145 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
50 °C

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-70c06149320242169d141ae7bf792bb2
Source dataset
uspto-grants-1985_06
Patent number
US04522828

Reaction notes

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