3-(3-Methoxypropoxy)-1-propanol → Ethyl 1-(2-methyl-4-quinolyl)piperidine-4-carboxylate

HRID 333936

Reaction equation

HRID 333936 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[CH:3]=1.[NH:13]1[CH2:18][CH2:17][CH:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]1.COCCCOCCCO>>[CH3:12][C:4]1[CH:3]=[C:2]([N:13]2[CH2:18][CH2:17][CH:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

4

Reactant 3

HCID 669843-(3-Methoxypropoxy)-1-propanolHCID 70770Ethyl 4-piperidinecarboxylateHCID 779734-Chloro-2-methylquinoline

Product 1

HCID 66835649Ethyl 1-(2-methyl-4-quinolyl)piperidine-4-carboxylateYield 162.9%

Conditions

Temperature
150 °C

Procedure

4-Chloroquinaldine (0.888 g, 5 mmol) and ethyl piperidine-4-carboxylate (1.18 g, 7.5 mmol) were mixed together with dipropyleneglycolmonomethylether (5 ml) and stirred at 150° C. for 48 hours. The solvent was removed under reduced pressure and the residue purified by column chromatography (pre-packed silica column, gradient of dichloromethane/ethyl acetate) to give 2.43 g of a brown oil that was used directly in the next step. MS (APCI): m/z=298.9 [M+1]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified by column chromatography (pre-packed silica column, gradient of dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-6ddc65aa77e64eb28cd472ecbc1001f7
Source dataset
uspto-grants-2014_11
Patent number
US08883791B2

Linked notes

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