Aluminium lithium hydride → (3-Phenoxypropyl)amine

HRID 6715Notes

Reaction equation

HRID 6715 reaction equation
[O:1]([CH2:8][CH2:9][C:10]([NH2:12])=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>[O:1]([CH2:8][CH2:9][CH2:10][NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 232735523-Phenoxypropanamide

Product 1

HCID 418237(3-Phenoxypropyl)amineYield 60.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 3-phenoxy-propionamide (1.0 g, 6.0 mmol) in diethyl ether (30 mL) was cooled to 0 C. Lithium aluminum hydride (0.46 g, 12 mmol) was added in portions to the stirring amide solution. The resulting slurry was allowed to warm to rt and stirred for 20 h. The mixture was cooled to 0° C. and carefully quenched by the sequential addition of 0.5 mL of water, followed by 0.5 mL of 3 N sodium hydroxide and 1.5 mL of water. The mixture was stirred for 15 min, then filtered to remove the aluminum salts. The filtrate was collected and the volatile material was removed by a rotary evaporator to give 3-phenoxy-propylamine (0.55 g) as a pale green oil.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customcarefully quenched by the sequential addition of 0.5 mL of water
  3. stirringThe mixture was stirred for 15 min
  4. filtrationfiltered
  5. customto remove the aluminum salts
  6. customThe filtrate was collected
  7. customthe volatile material was removed by a rotary evaporator

Sources & evidence

ORD record
ord-cdf5e48caf8840a28491872246f93c94
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Reaction notes

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