HCID 17980377, compound → (1-methylpiperidin-4-yl)(pyridin-2-yl)methanone

HRID 404243Notes

Reaction equation

HRID 404243 reaction equation
Br[CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[O:9])[NH:3]1.N.C(O)CO>>[CH3:16][N:13]1[CH2:14][CH2:15][CH:10]([C:8]([C:4]2[N:3]=[CH:2][CH:7]=[CH:6][CH:5]=2)=[O:9])[CH2:11][CH2:12]1

Participants

3

Reactant 2

HCID 17980377HCID 17980377, compoundHCID 22053026HCID 22053026, compound

Product 1

HCID 11321671(1-methylpiperidin-4-yl)(pyridin-2-yl)methanoneYield 128.2%

Conditions

Temperature
85 °C

Procedure

Load 2-bromo-6-(1-methylpiperidin-4-ylcarbonyl)-piperidine (20 g, 70.67 mmol, 1 eq) in 73.6 ml of 7M NH3/ethylene glycol (530 mmol, 7.5 eq) into a 130 ml pressure autoclave, and add Cu2O (101 mg, 0.706 mmol, 0.01 eq) as a catalyst. Seal the autoclave and heat the reaction mixture to 85° C. at about 50 psi (345 kPa) for 20 hrs. Cool the reaction mixture to room temperature, transfer the organic layer to a 250 ml flask, and place the flask under reduce pressure to remove ammonia. Add water (70 mL) and of 30% NaOH (38 mL) and then extract the mixture with methyl t-butyl ether (MTBE)(5×100 ml). Combine the organic fractions and then dry with MgSO4, filter, and concentrate under reduce pressure to obtain crude 2-amino-(6-(1-methylpiperidin-4-ylcarbonyl)-pyridine (18.5 g).

Workup

  1. customSeal the autoclave
  2. temperatureCool the reaction mixture to room temperature
  3. customto remove ammonia
  4. extractionAdd water (70 mL) and of 30% NaOH (38 mL) and then extract the mixture with methyl t-butyl ether (MTBE)(5×100 ml)
  5. dry with materialCombine the organic fractions and then dry with MgSO4
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-fc8a8fdf11594d549f91f133a2f1848f
Source dataset
uspto-grants-2014_06
Patent number
US08748459B2

Reaction notes

Loading…