Water → HCID 20540392, compound

HRID 596159Notes

Reaction equation

HRID 596159 reaction equation
[OH:1][C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][C:4]#[N:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[OH:1][C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][CH2:4][NH2:5]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 2660763-Hydroxy-3,3-diphenylpropanenitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 20540392HCID 20540392, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

35.5 g of β-hydroxy-β,β-diphenyl-propionitrile are added portionwise to the stirred suspension of 12.9 g of lithium aluminum hydride in 800 ml of diethyl ether while cooling with an ice bath. After stirring for 15 hours at room temperature and 2 hours at the boil, it is cooled again and 12.9 ml of water, 12.9 ml of 15% aqueous sodium hydroxide and 38.7 ml of water are added in this order. The mixture is filtered, the residue washed 3 times with 150 ml of methylene chloride, the filtrate dried, evaporated and the residue recrystallized from ethanol, to yield the 3-hydroxy-3,3-diphenyl-propylamine melting at 134°-136°.

Workup

  1. temperaturewhile cooling with an ice bath
  2. temperatureis cooled again
  3. filtrationThe mixture is filtered
  4. washthe residue washed 3 times with 150 ml of methylene chloride
  5. customthe filtrate dried
  6. customevaporated
  7. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-ef3b6463d6864801a6c0de16028c5bba
Source dataset
uspto-grants-1977_03
Patent number
US04010166

Reaction notes

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