Diethyl Ether → HCID 19823627, compound

HRID 1650964Notes

Reaction equation

HRID 1650964 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]=[CH:6][C:7]=1[Cl:8].[CH2:15]([Mg]Br)[CH2:16][CH:17]=[CH2:18].CCOCC.[BH4-].[Na+]>C(O)C.O.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH:13]([NH2:14])[CH2:18][CH2:17][CH:16]=[CH2:15])[CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 4311764Sodium borohydrideHCID 108571341-(3,4-Dichlorophenyl)-1-cyclobutane-carbonitrileHCID 178418797HCID 178418797, compound

Product 1

HCID 19823627HCID 19823627, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

1-(3,4-Dichlorophenyl)cyclobutanecarbonitrile (13 g) was added to a solution of 3-butenylmagnesium bromide [prepared from 4-bromobut-1-en (10.6 g), magnesium (2 g) and ether (65 ml)]. The ether was replaced by toluene (60 ml) and the mixture heated for 21/2 hours. The mixture was then added to a solution of sodium borohydride (4.4 g) in ethanol (200 ml). The mixture was heated under reflux for one hour, cooled, added to water and the resulting mixture extracted with ether. The extract yielded 1-[1-(3,4-dichlorophenyl)cyclobutyl]pent-4-enylamine as an oil. This oil was added to a 1N solution of sodium dihydrogen phosphite [287 ml-prepared by mixing a solution of phosphorous acid (41 g) in water (100 ml) with sodium bicarbonate (42 g) and making the resulting solution up to 500 ml with water]. Methanol (350 ml) and 37-40% aqueous formaldehyde (25 ml) were added and the mixture heated under reflux for 11/2 hours and was then allowed to stand for 21/2 days. The methanol was removed by evaporation and the aqueous residue extracted with ether. The ether extract yielded an oil which was dissolved in ether. The solution was filtered and treated with an ethereal solution of maleic acid. An oil formed which was triturated with ether to give a semi-solid which was basified to give a N,N-dimethyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]pent-4-enylamine.

Workup

  1. temperaturethe mixture heated for 21/2 hours
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for one hour
  4. temperaturecooled
  5. extractionthe resulting mixture extracted with ether

Sources & evidence

ORD record
ord-96b962d2213e4ad29cc3af4c711d948c
Source dataset
uspto-grants-1990_05
Patent number
US04925879

Reaction notes

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