Water → 2-Phenoxy-1-propanamine

HRID 1288230Notes

Reaction equation

HRID 1288230 reaction equation
[O:1]([CH:8]([CH3:11])[C:9]#[N:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[O:1]([CH:8]([CH3:11])[CH2:9][NH2:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 190944362-PhenoxypropanenitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 37183552-Phenoxy-1-propanamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2-phenoxypropionitrile (11.0 s.) in dry ether (50 ml.) was added dropwise to a stirred suspension of lithium aluminium hydride (3.8 g.) in dry ether (50 ml.). The mixture was then heated to reflux for 3 hours, cooled and treated cautiously (vigorous stirring) with water (3.8 ml.) then with 15% aqueous sodium hydroxide (3.8 ml.) and finally with water (11.4 ml.). The mixture was stirred for 20 minutes and filtered. The filtrate was dried over anhydrous potassium carbonate and evaporated. The residue was distilled under water-pump vacuum to give pure 2-phenoxypropylamine, b.p. 115°-116°/15 mm.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 3 hours
  3. temperaturecooled
  4. additiontreated cautiously
  5. filtrationfiltered
  6. dry with materialThe filtrate was dried over anhydrous potassium carbonate
  7. customevaporated
  8. distillationThe residue was distilled under water-pump vacuum

Sources & evidence

ORD record
ord-6a922e13d3f2425987de5b5a5296ee3b
Source dataset
uspto-grants-1976_10
Patent number
US03987158

Reaction notes

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