Piperidine → 5-(1-Piperidinylmethyl)-8-quinolinol

HRID 23938Notes

Reaction equation

HRID 23938 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:8][C:9]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]2[C:10]=1[CH:11]=[CH:12][CH:13]=[N:14]2>C(Cl)(Cl)Cl>[N:1]1([CH2:8][C:9]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]3[C:10]=2[CH:11]=[CH:12][CH:13]=[N:14]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 4168815-(Chloromethyl)quinolin-8-ol

Product 1

HCID 2796195-(1-Piperidinylmethyl)-8-quinolinolYield 50.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Piperidine (2 ml; 20.26 mmol) was added to a solution of 5-chloromethyl-8-hydroxyquinoline (1.87 g; 8.13 mmol) in CHCl3 (50 ml) at 5° C. The mixture was stirred for two days at room temperature. Then the mixture was evaporated under vacuum to dryness. The residue was dissolved in CHCl3, washed with 5% NaHCO3 (2×50 ml), followed by brine (50 ml), dried over Na2SO4 and evaporated to dryness. The residue was crystallized from hexane to give 1.0 g of the title product (50%). M.p. 96° C. TLC (CHCl3; MeOH; NH3=8:2:0.5). Rf=0.63.

Workup

  1. customThen the mixture was evaporated under vacuum to dryness
  2. dissolutionThe residue was dissolved in CHCl3
  3. washwashed with 5% NaHCO3 (2×50 ml)
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-8d29bf5684da4adfb760c88a306ae797
Source dataset
uspto-grants-2005_02
Patent number
US06855711B1

Reaction notes

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