Hydrochloric Acid → 5-Piperazinomethyl-8-hydroxyquinoline trichloride

HRID 23943Notes

Reaction equation

HRID 23943 reaction equation
[ClH:1].C([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]3[C:12]=2[CH:13]=[CH:14][CH:15]=[N:16]3)[CH2:6][CH2:5]1)=O>CO>[Cl-:1].[Cl-:1].[Cl-:1].[N:7]1([CH2:10][C:11]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]3[C:12]=2[CH:13]=[CH:14][CH:15]=[N:16]3)[CH2:8][CH2:9][NH:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 97954545-(4-Formylpiperazinomethyl)-8-hydroxyquinoline

Product 1

HCID 225698165-Piperazinomethyl-8-hydroxyquinoline trichloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of ˜16% HCl in methanol (25 ml) was added to a solution of compound 23 (300 ng, 1.23 mmol) in absolute methanol (5 ml). (Upon addition of the acid, all insoluble material was dissolved). The reaction mixture was stirred at room temperature. After 10 min, a yellow powder was precipitated; the mixture was stirred overnight. The product was then filtered and washed with absolute methanol (5 ml×2). The product was obtained as a yellow powder in quantitative yield. TLC and the m.p. showed the product to be identical to that obtained previously.

Workup

  1. addition(Upon addition of the acid
  2. dissolutionall insoluble material was dissolved)
  3. customa yellow powder was precipitated
  4. stirringthe mixture was stirred overnight
  5. filtrationThe product was then filtered
  6. washwashed with absolute methanol (5 ml×2)
  7. customThe product was obtained as a yellow powder in quantitative yield
  8. customthat obtained previously

Sources & evidence

ORD record
ord-00f79118668e43aa9bf044202e639d8c
Source dataset
uspto-grants-2005_02
Patent number
US06855711B1

Reaction notes

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