Potassium Carbonate → HCID 66805420, compound

HRID 1193390Notes

Reaction equation

HRID 1193390 reaction equation
[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].Cl[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([C:23]#[N:24])[CH:18]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[C:23]([C:19]1[CH:18]=[C:17]([N:13]2[CH2:12][CH2:11][CH:10]([N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:6])[CH3:7])[CH2:15][CH2:14]2)[CH:22]=[CH:21][N:20]=1)#[N:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6933424-Chloro-2-pyridinecarbonitrileHCID 27568064-N-Boc-4-N-Methyl-aminopiperidine

Product 1

HCID 66805420HCID 66805420, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butyl methyl(piperidin-4-yl)carbamate (465 mg, 2.173 mmol, 1.0 eq.), 4-chloropyridine-2-carbonitrile (300 mg, 2.173 mmol, 1.0 eq.) and K2CO3 (600 mg, 4.34 mmol, 2.0 eq.) in THF (4 ml) was heated for 48 hours at 100° C. in a pressure vessel. The mixture was filtered and washed with THF (10 ml). The filtrate was concentrated and purified by column chromatography (silica gel, 1% MeOH in DCM). Yield: 44% (300 mg, 0.949 mmol)

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with THF (10 ml)
  3. concentrationThe filtrate was concentrated
  4. custompurified by column chromatography (silica gel, 1% MeOH in DCM)

Sources & evidence

ORD record
ord-71b2f800469f496ca03cd6ddaa0792df
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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