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Hydrochloric Acid → 4-[[3-(p-Chlorophenyl)propyl]methylamino]benzoic acid

HRID 1154355
Notes
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Reaction equation

HRID 1154355 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]([CH3:23])[C:12]2[CH:22]=[CH:21][C:15]([C:16]([O:18]CC)=[O:17])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C(O)C.[OH-].[K+].Cl>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][N:11]([CH3:23])[C:12]2[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:21][CH:22]=2)=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 442788874-[[3-(p-Chlorophenyl)propyl]methylamino]benzoic acid, ethyl ester

Product 1

HCID 442788864-[[3-(p-Chlorophenyl)propyl]methylamino]benzoic acid

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

A 1.80 g. portion of 4-[[3-(p-chlorophenyl)propyl]methylamino]benzoic acid, ethyl ester is dissolved in 15 ml. of 95% ethanol. A 1 g. portion of potassium hydroxide is added, and the mixture is refluxed overnight. The solution is poured into 30 ml. of water, the pH is adjusted to 6 using 37% hydrochloric acid, and the solid is collected and dried. This solid is dissolved in benzene, filtered, and evaporated, giving 750 mg. of the desired product.

Workup

  1. temperaturethe mixture is refluxed overnight
  2. additionThe solution is poured into 30 ml
  3. customthe solid is collected
  4. customdried
  5. dissolutionThis solid is dissolved in benzene
  6. filtrationfiltered
  7. customevaporated
  8. customgiving 750 mg

Sources & evidence

ORD record
ord-88abf7045b4d488ab11c42876ca3fc58
Source dataset
uspto-grants-1984_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04489094

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes