Diethyl Ether → N-benzyl-3-hydroxy-3,3-diphenylpropylamine

HRID 372787Notes

Reaction equation

HRID 372787 reaction equation
[C:1]([NH:9][CH2:10][CH2:11][C:12]([OH:25])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[OH-].[Na+]>O>[CH2:1]([NH:9][CH2:10][CH2:11][C:12]([OH:25])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 14116453N-(3-Hydroxy-3,3-diphenylpropyl)benzamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 20326648N-benzyl-3-hydroxy-3,3-diphenylpropylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

72.3 g of N-benzoyl-3-hydroxy-3,3-diphenylpropylamine are added portionwise to the suspension of 16.3 g of lithium aluminum hydride in 1.6 lt of diethyl ether while stirring and cooling with an ice-bath. The mixture is stirred for 2 hours while warming to room temperature and 3 hours while refluxing. It is cooled again and 16.3 g of water, 16.3 ml of 15% aqueous sodium hydroxide and 49 ml water are added in this order, filtered and the residue washed 3 times with 300 ml of warm chloroform. The combined filtrates are dried and evaporated, to yield the N-benzyl-3-hydroxy-3,3-diphenylpropylamine melting at 145°-146°.

Workup

  1. temperaturecooling with an ice-bath
  2. stirringThe mixture is stirred for 2 hours
  3. temperaturewhile refluxing
  4. temperatureIt is cooled again
  5. filtrationfiltered
  6. washthe residue washed 3 times with 300 ml of warm chloroform
  7. customThe combined filtrates are dried
  8. customevaporated

Sources & evidence

ORD record
ord-dec7dae81e6a4281971de0a41abf4f08
Source dataset
uspto-grants-1978_05
Patent number
US04092330

Reaction notes

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