Hydrochloric Acid → HCID 64222602, compound

HRID 1727194Notes

Reaction equation

HRID 1727194 reaction equation
[CH3:1][C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH2:7][NH:6][C:5](=O)[CH2:4][CH2:3]1.O1CCCC1.B.Cl>O1CCCC1>[NH3:6].[CH3:1][C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH2:3][CH2:4][CH2:5][NH:6][CH2:7]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 69058444HCID 69058444, compound

Product 2

HCID 222AmmoniaHCID 64222602HCID 64222602, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a dried flask under nitrogen was added borane tetrahydrofuran complex (1 M solution, 8.79 ml, 8.79 mmol), and tetrahydrofuran (10 ml). The solution was cooled to 0° C. and a solution of 5-methyl-5-(2-pyridinyl)-2-piperidone (Preparation 41, 1 g, 5.26 mmol) in tetrahydrofuran (20 ml) was added. The reactants were warmed to room temperature and then heated at reflux for 6 h. Further borane tetrahydrofuran, complex (1M solution, 8.79 ml, 8.79 mmol) was added and the reaction mixture was heated at reflux for 18 h. Thin layer chromatography still showed starting material was present so further borane tetrahydrofuran complex (1M solution, 8.79 ml, 8.79 mmol) was added and the reaction mixture was heated under reflux for 18 h. Upon completion hydrochloric acid (6M) was added to the reaction mixture and the mixture was stirred for 30 min. The reaction mixture was partially concentrated before adjusting to pH 11 with solid sodium hydroxide. The organic extracts were extracted with dichloromethane (5×20 ml) and dried (Na2SO4) to give a crude oil (0.45 g). The oil was purified by flash chromatography eluting with dichloromethane:methanol:0.88 ammonia solution (94:4:2) to give the title compound as an oil (0.20 g, 22%).

Workup

  1. temperatureThe reactants were warmed to room temperature
  2. temperatureheated
  3. temperatureat reflux for 6 h
  4. temperaturethe reaction mixture was heated
  5. temperatureat reflux for 18 h
  6. additionwas added
  7. temperaturethe reaction mixture was heated
  8. temperatureunder reflux for 18 h
  9. concentrationThe reaction mixture was partially concentrated
  10. extractionThe organic extracts were extracted with dichloromethane (5×20 ml)
  11. dry with materialdried (Na2SO4)
  12. customto give a crude oil (0.45 g)
  13. customThe oil was purified by flash chromatography
  14. washeluting with dichloromethane

Sources & evidence

ORD record
ord-8d4a154a770244a0ac9cc7da20f197ca
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

Loading…