Potassium Carbonate → 4,4-Diphenylbutylamine

HRID 542427Notes

Reaction equation

HRID 542427 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][CH2:15][C:16]#[N:17])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>CCOCC.O1CCOCC1.O>[C:18]1([CH:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:14][CH2:15][CH2:16][NH2:17])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 896104,4-DiphenylbutyronitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 30158634,4-Diphenylbutylamine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of lithium aluminum hydride (23 g) in ether (1 L) is added a solution of 4,4-diphenylbutyronitrile in dioxane (6.25 L), dropwise, at a rate causing gentle reflux. The reaction is maintained at reflux for one hour, and then a solution of potassium carbonate (200 g) in water (300 mL) is added dropwise with stirring. The mixture is filtered with a 1/1 dioxane/ether wash, and evaporation in vacuo of the filtrate followed by distillation affords the title compound (76 g), bp 145°-150° C. at 0.6 mm. The free amine is generally converted to the hydrobromide salt prior to use.

Workup

  1. temperatureThe reaction is maintained
  2. temperatureat reflux for one hour
  3. filtrationThe mixture is filtered with a 1/1 dioxane/ether
  4. washwash
  5. customevaporation in vacuo of the filtrate
  6. distillationfollowed by distillation

Sources & evidence

ORD record
ord-c78ce6cbf0ca4ef5817c12708c385e8a
Source dataset
uspto-grants-1987_04
Patent number
US04657898

Reaction notes

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