Water → HCID 20225031, compound

HRID 1249167Notes

Reaction equation

HRID 1249167 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].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:13][NH2:14])[CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 108571341-(3,4-Dichlorophenyl)-1-cyclobutane-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 20225031HCID 20225031, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1-(3,4-dichlorophenyl)-1-cyclobutanecarbonitrile (28.5 g) in dry ether (200 ml) was added dropwise in a nitrogen atmosphere to a stirred mixture of lithium aluminium hydride (6.5 g) and dry ether (200 ml). The mixture was stirred at room temperature for two hours then it was cooled to 10° C. Water (12 ml) and then 15% aqueous sodium hydroxide solution (12 ml) and then water (36 ml) were added. The mixture was filtered through diatomaceous earth (trade name CELITE). The filter was washed with ether and the combined ether phases were washed with water and dried. Hydrogen chloride gas was passed into the solution to give [1-(3,4-dichlorophenyl)cyclobutyl]methylamine hydrochloride (m.p. 271°-272° C.).

Workup

  1. temperatureit was cooled to 10° C
  2. filtrationThe mixture was filtered through diatomaceous earth (trade name CELITE)
  3. washThe filter was washed with ether
  4. washthe combined ether phases were washed with water
  5. customdried

Sources & evidence

ORD record
ord-3acdf8d4e6f54bd7bb167f5f6049c62a
Source dataset
uspto-grants-1986_12
Patent number
US04629727

Reaction notes

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