Hydrochloric Acid → HCID 68145786, compound

HRID 1730166Notes

Reaction equation

HRID 1730166 reaction equation
[CH3:1][C:2]1([CH3:23])[NH:6][C@@H:5]([C:7]2[CH:16]=[CH:15][C:10]([NH:11]C(=O)C)=[CH:9][CH:8]=2)[CH2:4][C@@H:3]1[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.[OH-].[K+].[ClH:26]>C(O)C>[ClH:26].[ClH:26].[ClH:26].[NH2:11][C:10]1[CH:15]=[CH:16][C:7]([C@@H:5]2[NH:6][C:2]([CH3:23])([CH3:1])[C@@H:3]([C:17]3[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=3)[CH2:4]2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 12621399HCID 12621399, compound

Product 1

HCID 68145786HCID 68145786, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.18 G. of 4'-[trans-5,5-dimethyl-4-(4-pyridyl)-2-pyrrolidinyl]-acetanilide are treated with a solution of 0.18 g. of potassium hydroxide in 1.8 ml. of ethanol and boiled under reflux for 48 hours. The resulting reaction mixture is then evaporated under reduced pressure and the residue is treated with water and extracted three times with methylene chloride. The organic phase is dried over sodium sulfate and evaporated under reduced pressure. The residue which results is treated with ethereal HCl and crystallized with ethanol/ether to yield 4-[trans-5-(p-aminophenyl)-2,2-dimethyl-3-pyrrolidinyl]-pyridine trihydrochloride of melting point 240°-242° C.

Workup

  1. temperatureunder reflux for 48 hours
  2. customThe resulting reaction mixture
  3. customis then evaporated under reduced pressure
  4. additionthe residue is treated with water
  5. extractionextracted three times with methylene chloride
  6. dry with materialThe organic phase is dried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue which results
  9. customcrystallized with ethanol/ether

Sources & evidence

ORD record
ord-4b2c20dc63284b76bc6880abfa6e634b
Source dataset
uspto-grants-1976_11
Patent number
US03991197

Reaction notes

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