Water → {2,7-Dichloro-6-methyl-4-[(4-methylpiperidin-1-yl)methyl]quinolin-3-yl}methanol

HRID 720507Notes

Reaction equation

HRID 720507 reaction equation
[Cl:1][C:2]1[C:11]([CH2:12][OH:13])=[C:10]([CH2:14]Cl)[C:9]2[C:4](=[CH:5][C:6]([Cl:17])=[C:7]([CH3:16])[CH:8]=2)[N:3]=1.[CH3:18][CH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.O.ClC(Cl)C>C1COCC1>[Cl:1][C:2]1[C:11]([CH2:12][OH:13])=[C:10]([CH2:14][N:22]2[CH2:23][CH2:24][CH:19]([CH3:18])[CH2:20][CH2:21]2)[C:9]2[C:4](=[CH:5][C:6]([Cl:17])=[C:7]([CH3:16])[CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 63651,1-DichloroethaneHCID 693814-MethylpiperidineHCID 15521700HCID 15521700, compound

Product 1

HCID 15521697{2,7-Dichloro-6-methyl-4-[(4-methylpiperidin-1-yl)methyl]quinolin-3-yl}methanolYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product of Stage 82.d (16.2 g; 55.7 mmol) in THF (70 ml) is treated with a solution of 4-methylpiperidine (23 ml; 195 mmol). The mixture obtained is agitated at ambient temperature for 2 hours. Water (200 ml) and dichloroethane (200 ml) are added. The organic phase is washed with an aqueous solution of sodium chloride (concentrated to 20% by weight; 100 ml), dried over magnesium sulphate and concentrated under reduced pressure. By crystallization of the residue from diethylether, the product in the title is obtained (18.3 g; 93% yield) in the form of a white crystalline solid (M.p. 170–171,5° C.).

Workup

  1. customThe mixture obtained
  2. washThe organic phase is washed with an aqueous solution of sodium chloride (concentrated to 20% by weight; 100 ml)
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customBy crystallization of the residue from diethylether

Sources & evidence

ORD record
ord-9ac6655163cd47d2bc4ce27a4176cecc
Source dataset
uspto-grants-2006_11
Patent number
US07135478B2

Reaction notes

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