Hydrochloric Acid → 1-Benzylpiperidine-4-acetonitrile

HRID 126861Notes

Reaction equation

HRID 126861 reaction equation
[C:1]([CH:3]([CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)C(OCC)=O)#[N:2].[OH-].[Na+].Cl>>[C:16]1([CH2:15][N:12]2[CH2:13][CH2:14][CH:9]([CH2:3][C:1]#[N:2])[CH2:10][CH2:11]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14989188Ethyl alpha-cyano-1-(phenylmethyl)-4-piperidineacetate

Product 1

HCID 5624991-Benzylpiperidine-4-acetonitrileYield 82%

Procedure

A mixture of 58 parts of ethyl α-cyano-1-(phenylmethyl)-4-piperidineacetate and 125 parts of sodium hydroxide solution 2 N is stirred for 3 hours at room temperature. The mixture is neutralized with concentrated hydrochloric acid while cooling and the solvent is evaporated. The residue is stirred for 4 hours at 150° C. in 180 parts of N,N-dimethylacetamide. The reaction mixture is cooled, filtered and the filtrate is evaporated. The residue is taken up in water and extracted with methylbenzene. The extract is dried, filtered and evaporated. The residue is distilled, yielding 35 parts (82%) of 1-(phenylmethyl)-4-piperidineacetonitrile; bp. 135°-140° C. at 0.2-0.3 mm. pressure.

Workup

  1. temperaturewhile cooling
  2. customthe solvent is evaporated
  3. stirringThe residue is stirred for 4 hours at 150° C. in 180 parts of N,N-dimethylacetamide
  4. temperatureThe reaction mixture is cooled
  5. filtrationfiltered
  6. customthe filtrate is evaporated
  7. extractionextracted with methylbenzene
  8. customThe extract is dried
  9. filtrationfiltered
  10. customevaporated
  11. distillationThe residue is distilled

Sources & evidence

ORD record
ord-a6cd05033ae94af7b28d883d7f3f3e52
Source dataset
uspto-grants-1981_03
Patent number
US04254127

Reaction notes

Loading…