Diethyl Ether → HCID 15746783, compound

HRID 620187Notes

Reaction equation

HRID 620187 reaction equation
[NH2-].[Na+].CCOCC.[Cl:8][C:9]1[CH:10]=[C:11]([CH2:16][C:17]#[N:18])[CH:12]=[CH:13][C:14]=1[Cl:15].[CH2:19]([CH:26]1[CH2:31][CH2:30][N:29]([CH2:32][CH2:33]Cl)[CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O>[CH2:19]([CH:26]1[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][CH:16]([C:11]2[CH:12]=[CH:13][C:14]([Cl:15])=[C:9]([Cl:8])[CH:10]=2)[C:17]#[N:18])[CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24533Sodium amideHCID 76690(3,4-Dichlorophenyl)acetonitrileHCID 15870313HCID 15870313, compound

Product 1

HCID 15746783HCID 15746783, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.95 g of sodium amide are added in small quantities to an ether solution of 9.3 g of 3,4-dichlorophenylacetonitrile. The mixture is heated for 2 hours to reflux, 11.8 g of 2-(4-benzylpiperidino)-1-chloro ethane are added and heating is repeated for another 5 hours to reflux. The resulting mixture is cooled and 200 ml of water are added, after what the organic phase is decanted, washed with water and extracted with a 10% solution of hydrochloric acid. The aqueous phase is then neutralized with soda, extracted with ether, washed with water, dried over magnesium sulfate and evaporated. 13 g of oily product are thus obtained.

Workup

  1. temperatureThe mixture is heated for 2 hours
  2. temperatureto reflux
  3. temperatureheating
  4. temperatureto reflux
  5. temperatureThe resulting mixture is cooled
  6. customafter what the organic phase is decanted
  7. washwashed with water
  8. extractionextracted with a 10% solution of hydrochloric acid
  9. extractionextracted with ether
  10. washwashed with water
  11. dry with materialdried over magnesium sulfate
  12. customevaporated

Sources & evidence

ORD record
ord-86d15fb1149849e59f5980f320f7c63e
Source dataset
uspto-grants-1989_04
Patent number
US04820717

Reaction notes

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