Hydrochloric Acid → 1-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-(4-carbamylphenyl)urea dihydrochloride

HRID 1380210

Reaction equation

HRID 1380210 reaction equation
[OH2:1].[ClH:2].Cl.[Cl:4][C:5]1[CH:32]=[CH:31][C:8]([CH2:9][N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][NH:19][C:20]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=3)=[O:21])[CH2:12][CH2:11]2)=[CH:7][CH:6]=1.Cl.[OH-].[K+]>C(O)(=O)C>[ClH:4].[ClH:2].[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][NH:19][C:20]([NH:22][C:23]3[CH:24]=[CH:25][C:26]([C:29](=[O:1])[NH2:30])=[CH:27][CH:28]=3)=[O:21])[CH2:14][CH2:15]2)=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 202057271-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-(4-cyanophenyl)urea dihydrochloride monohydrate

Product 1

HCID 136067101-{3-[4-(4-Chlorobenzyl)piperazin-1-yl]propyl}-3-(4-carbamylphenyl)urea dihydrochlorideYield 70.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1-{3-[4-(4-chlorobenzyl)piperazin-1-yl]propyl}-3-(4-cyanophenyl)urea dihydrochloride monohydrate (10.0 g; 19.9 mmole), glacial acetic acid (120 ml), and concentrated hydrochloric acid (80 ml) was heated at 80° C. for 30 minutes. The mixture was then poured over ice, and basified with aqueous potassium hydroxide. The product was extracted with methylene chloride, dried (sodium sulfate), and the salt precipitated out ethereal hydrochloric acid. Several recrystallizations from ethanol provided the title compound (3.54 g; 38% yield) as colorless crystals, m.p. 224°-226° C.

Workup

  1. additionThe mixture was then poured over ice
  2. extractionThe product was extracted with methylene chloride
  3. dry with materialdried (sodium sulfate)
  4. customthe salt precipitated out ethereal hydrochloric acid
  5. customSeveral recrystallizations from ethanol

Sources & evidence

ORD record
ord-dc5254fe08fc4212b6cf184629055ef2
Source dataset
uspto-grants-1986_04
Patent number
US04579947

Linked notes

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