Hydrochloric Acid → HCID 69871477, compound

HRID 1977906Notes

Reaction equation

HRID 1977906 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:21])=[CH:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][C:16](C=O)=[CH:15][CH:14]=2)[N:8]=1.O1CCN(C2CCC=CC2)CC1.[C:34]12(CS(O)(=O)=O)[C:41](C)(C)[CH:38](C[CH2:40]1)[CH2:37][C:35]2=[O:36].Cl>C(OCC)(=O)C.O.C1C=CC=CC=1>[CH3:1][C:2]1[NH:3][C:4]([CH3:21])=[CH:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:14]=[CH:15][C:16]([CH:40]=[C:34]3[CH2:41][CH2:38][CH2:37][C:35]3=[O:36])=[CH:17][CH:18]=2)[N:8]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 21995425HCID 21995425, compoundHCID 54394888HCID 54394888, compound

Product 1

HCID 69871477HCID 69871477, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a 100 mL round-bottomed flask equipped with Dean-Stark trap topped with a condenser and N2 inlet were added 552 mg (2.0 mmol) 2-(2,5-dimethylpyrrolyl)-6-(4-formylphenyl)-pyridine, 20 mL benzene, 0.384 mL (2.4 mmol) 4-morpholino-1-cyclohexene, and 10 mg camphorsulfonic acid. The solution was refluxed with removal of water for 13 hours cooled, and 25 mL 3N hydrochloric acid added. The mixture was stirred at room temperature for 1 hour then diluted with ethyl acetate and water. The organic layer was separated, washed with aqueous sodium bicarbonate solution and brine, dried over sodium sulfate, and evaporated. The crude oil solidified on standing, 460 mg (˜100%), and was used directly in the next step.

Workup

  1. customTo a 100 mL round-bottomed flask equipped with Dean-Stark trap
  2. customtopped with a condenser and N2 inlet
  3. temperaturecooled
  4. customThe organic layer was separated
  5. washwashed with aqueous sodium bicarbonate solution and brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-afe84c47f35e48d3be55b4330e97df74
Source dataset
uspto-grants-2001_05
Patent number
US06235750B1

Reaction notes

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