Diethyl Ether → HCID 20368531, compound

HRID 616648Notes

Reaction equation

HRID 616648 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[Cl:12][C:13]1[CH:14]=[C:15]([CH:20]([CH:26]([N:28]([CH3:30])[CH3:29])[CH3:27])[C:21](OCC)=[O:22])[CH:16]=[CH:17][C:18]=1[Cl:19]>O>[Cl:12][C:13]1[CH:14]=[C:15]([CH:20]([CH:26]([N:28]([CH3:30])[CH3:29])[CH3:27])[CH2:21][OH:22])[CH:16]=[CH:17][C:18]=1[Cl:19]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 20368563HCID 20368563, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20368531HCID 20368531, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 10 g. of lithium aluminum hydride in 300 ml. of diethyl ether, 18.7 g. of ethyl 2-(3,4-dichlorophenyl)-3-dimethylaminobutyrate is added dropwise with stirring. The mixture is refluxed for 40-45 hours and after cooling with an ice bath, 50 ml. of water is added very slowly. After filtering off and thoroughly washing out the inorganic salts, the dried organic filtrate is evaporated and the residue is distilled in vacuo at 115° C/0.4 mm Hg to yield 13 g. of the title compound. The hydrochloride salt melts at 188°-190° C.

Workup

  1. additionTo a suspension of 10 g
  2. temperatureThe mixture is refluxed for 40-45 hours
  3. temperatureafter cooling with an ice bath
  4. filtrationAfter filtering off
  5. washthoroughly washing out the inorganic salts
  6. customthe dried organic filtrate is evaporated
  7. distillationthe residue is distilled in vacuo at 115° C/0.4 mm Hg
  8. customto yield 13 g

Sources & evidence

ORD record
ord-5ea46f85c6274071bec4a1d366e40f8b
Source dataset
uspto-grants-1978_02
Patent number
US04075241

Reaction notes

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