Hydrochloric Acid → HCID 20382368, compound

HRID 1448349Notes

Reaction equation

HRID 1448349 reaction equation
[CH3:1][CH:2]([N:4]1[CH2:9][CH2:8][C:7]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:10]([O:12]CC)=[O:11])[CH2:6][CH2:5]1)[CH3:3].[OH-].[K+].Cl.[OH-].[Na+]>O.C(O)CO>[CH3:3][CH:2]([N:4]1[CH2:9][CH2:8][C:7]([NH:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([C:10]([OH:12])=[O:11])[CH2:6][CH2:5]1)[CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 20382350HCID 20382350, compound

Product 1

HCID 20382368HCID 20382368, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Procedure

A mixture of 43.6 parts of ethyl 1-(1-methylethyl)-4-(phenylamino)-4-piperidinecarboxylate, 25.5 parts of potassium hydroxide and 137.5 parts of 1,2-ethanediol is stirred and refluxed for 3 hours. The reaction mixture is cooled, poured onto 250 parts of water and acidified with a concentrated hydrochloric acid solution. The whole is alkalized and saturated with sodium hydroxide solution 50%. The precipitated product is filtered off and dissolved in 300 parts of water while heating. The solution is neutralized with acetic acid. The precipitated product is filtered off, washed with distilled water and suspended in 80 parts of 2-propanol. The product is filtered off and dried, yielding 27 parts (68.5%) of 1-(1-methylethyl)-4-(phenylamino)-4-piperidinecarboxylic acid; mp. 200° C.

Workup

  1. temperaturerefluxed for 3 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationThe precipitated product is filtered off
  4. dissolutiondissolved in 300 parts of water
  5. temperaturewhile heating
  6. filtrationThe precipitated product is filtered off
  7. washwashed with distilled water
  8. filtrationThe product is filtered off
  9. customdried

Sources & evidence

ORD record
ord-6a6a825887dc4f2fb68304af63ecca53
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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