Potassium Sodium Tartrate → 1-[1-(3,4-Dichlorophenyl)cyclobutyl]ethylamine

HRID 1382470Notes

Reaction equation

HRID 1382470 reaction equation
[C:1](=[N:15]O)([C:3]1([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=2)[CH2:6][CH2:5][CH2:4]1)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].[OH-].[Na+]>CCOCC.O>[Cl:14][C:9]1[CH:8]=[C:7]([C:3]2([CH:1]([NH2:15])[CH3:2])[CH2:6][CH2:5][CH2:4]2)[CH:12]=[CH:11][C:10]=1[Cl:13]

Participants

7

Reactant 4

HCID 9357Potassium Sodium TartrateHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 860311131-Acetyl-1-(3,4-dichlorophenyl)cyclobutane oxime

Product 1

HCID 130831401-[1-(3,4-Dichlorophenyl)cyclobutyl]ethylamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of the oxime prepared above (4.0 g) in ether (50 ml) was added slowly to a stirred suspension of lithium aluminium hydride (0.9 g) in ether (50 ml) under nitrogen. The mixture was heated under reflux for one hour and, after cooling, water and then a 20% aqueous solution of Rochelle's salt (potassium sodium tartrate tetrahydrate) (27 ml) and a 10% aqueous solution of sodium hydroxide (6 ml) added. The reaction mixture was stirred for one hour and then continuously extracted with ether during eighteen hours. The ether extract was dried and the ether removed to leave a solid from which 1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine was separated by high pressure liquid chromatography. The product was identified by standard analytical techniques as the compound of Example 1 in the form of its free base.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for one hour
  3. temperatureafter cooling
  4. extractioncontinuously extracted with ether during eighteen hours
  5. extractionThe ether extract
  6. customwas dried
  7. customthe ether removed

Sources & evidence

ORD record
ord-0cb90b02f4b5400e9f752d438fd09ad1
Source dataset
uspto-grants-1989_02
Patent number
US04806570

Reaction notes

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