Triethylamine → HCID 86694652, compound

HRID 63342Notes

Reaction equation

HRID 63342 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][O:8][C:9]2[N:14]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH2:3][CH2:2]1.CCN(CC)CC.Cl[C:27]([O:29][CH2:30][CH3:31])=[O:28]>C(Cl)Cl>[CH2:30]([O:29][C:27]([N:1]1[CH2:2][CH2:3][CH:4]([CH2:7][O:8][C:9]2[N:14]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:6]1)=[O:28])[CH3:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 89704554Methyl 6-(piperidin-4-ylmethoxy)picolinate

Product 1

HCID 86694652HCID 86694652, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of methyl 6-(piperidin-4-ylmethoxy)picolinate (0.3 g, 1.2 mmol), Et3N (0.2 g, 1.8 mmol) in DCM (10 ml) was added ethyl chloroformate (0.2 g, 1.8 mmol) at 0° C. The reaction was warmed to room temperature, washed with 1N HCl (20 ml), dried over Na2SO4 and concentrated under reduced pressure to give methyl 6-((1-(ethoxycarbonyl)piperidin-4-yl)methoxy)picolinate which used in the next step without further purification. Yield (0.38 g, quant.).

Workup

  1. washwashed with 1N HCl (20 ml)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-da5653d866724ed1b16b9b17b7b751fb
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Reaction notes

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