Hydrochloric Acid → HCID 21484874, compound

HRID 1414717Notes

Reaction equation

HRID 1414717 reaction equation
[C:1]1([C:7]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)(/[CH:10]=[CH:11]/[CH2:12][N:13]2[CH2:18][CH2:17][C:16]([C:25]([O:27]CC)=[O:26])([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[ClH:38]>CO>[ClH:38].[C:30]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(/[CH:10]=[CH:11]/[CH2:12][N:13]2[CH2:14][CH2:15][C:16]([C:25]([OH:27])=[O:26])([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:17][CH2:18]2)[C:8]#[N:9])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21484880HCID 21484880, compound

Product 1

HCID 21484874HCID 21484874, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.0 part 2,2-diphenyl-5-(4-ethoxycarbonyl-4-phenylpiperidino)-3-trans-pentenenitrile, 2.5 parts sodium hydroxide and 4.2 parts methanol is heated for 16 hours at reflux. Then, the solution is cooled and stripped in vacuo. The residue is suspended in ice-cold water, treated with excess aqueous hydrochloric acid, and extracted three times with portions of methylene chloride, resulting in a fine solid at the interface. This solid is collected by filtration, washed with water, air-dried and recrystallized from a methanolether mixture to afford 2,2-diphenyl-5-(4-carboxy-4-phenylpiperidino)-3-trans-pentenenitrile hydrochloride. This compound melts at about 266°-268° C. with gas evolution and is represented by the following structural formula. ##STR6##

Workup

  1. temperatureis heated for 16 hours
  2. temperatureat reflux
  3. temperatureThen, the solution is cooled
  4. extractionextracted three times with portions of methylene chloride
  5. customresulting in a fine solid at the interface
  6. filtrationThis solid is collected by filtration
  7. washwashed with water
  8. customair-dried
  9. customrecrystallized from a methanolether mixture

Sources & evidence

ORD record
ord-5a5dfe30796a4e52b7129f799508bda7
Source dataset
uspto-grants-1977_01
Patent number
US04002618

Reaction notes

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