Acetonitrile → Methyl 5-{[(4-{2-[1-(6-methylpyridin-2-yl)piperidin-4-yl]ethyl}piperidin-1-yl)carbonyl]oxy}nicotinate

HRID 605836Notes

Reaction equation

HRID 605836 reaction equation
[N+](C1C=CC(O[C:9]([O:11][C:12]2[CH:13]=[N:14][CH:15]=[C:16]([CH:21]=2)[C:17]([O:19][CH3:20])=[O:18])=[O:10])=CC=1)([O-])=O.C(#N)C.Cl.Cl.[CH3:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([N:36]2[CH2:41][CH2:40][CH:39]([CH2:42][CH2:43][CH:44]3[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]3)[CH2:38][CH2:37]2)[N:31]=1>CCOC(C)=O>[CH3:29][C:30]1[N:31]=[C:32]([N:36]2[CH2:41][CH2:40][CH:39]([CH2:42][CH2:43][CH:44]3[CH2:49][CH2:48][N:47]([C:9]([O:11][C:12]4[CH:13]=[N:14][CH:15]=[C:16]([CH:21]=4)[C:17]([O:19][CH3:20])=[O:18])=[O:10])[CH2:46][CH2:45]3)[CH2:38][CH2:37]2)[CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 57421835Methyl 5-{[(4-nitrophenoxy)carbonyl]oxy}nicotinateHCID 575078182-Methyl-6-[4-(2-piperidin-4-ylethyl)piperidin-1-yl]pyridine dihydrochloride

Product 1

HCID 57507820Methyl 5-{[(4-{2-[1-(6-methylpyridin-2-yl)piperidin-4-yl]ethyl}piperidin-1-yl)carbonyl]oxy}nicotinateYield 63%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 5-{[(4-nitrophenoxy)carbonyl]oxy}nicotinate (505 mg) was added to an acetonitrile (10 ml) solution of 2-methyl-6-[4-(2-piperidin-4-ylethyl)piperidin-1-yl]pyridine dihydrochloride (520 mg) and TEA (0.50 ml), followed by stirring at room temperature for 3 hours. The reaction liquid was diluted with EtOAc, washed with an aqueous saturated sodium hydrogencarbonate solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (eluent: chloroform:methanol=98:2 (v/v)) to obtain methyl 5-{[(4-{2-[1-(6-methylpyridin-2-yl)piperidin-4-yl]ethyl}piperidin-1-yl}carbonyl]oxy}nicotinate (424 mg).

Workup

  1. customThe reaction liquid
  2. washwashed with an aqueous saturated sodium hydrogencarbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe resulting residue was purified by silica gel column chromatography (eluent: chloroform:methanol=98:2 (v/v))

Sources & evidence

ORD record
ord-a22f4a9192c54e81b57f427f946d1d4b
Source dataset
uspto-grants-2011_03
Patent number
US07915261B2

Reaction notes

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