Potassium Carbonate → HCID 62141377, compound

HRID 227811Notes

Reaction equation

HRID 227811 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([Cl:18])=[N:10][N:9]=1.[NH:19]1[CH2:24][CH2:23][CH2:22][CH:21]([OH:25])[CH2:20]1>CS(C)=O>[Cl:18][C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([N:19]2[CH2:24][CH2:23][CH2:22][CH:21]([OH:25])[CH2:20]2)=[N:9][N:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 232933-HydroxypiperidineHCID 784901,4-Dichlorophthalazine

Product 1

HCID 62141377HCID 62141377, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
90 °C

Procedure

A resealable pressure bottle was charged with potassium carbonate (273 mg, 2.0 mmol), 1,4-dichlorophthalazine (590 mg, 3.0 mmol), piperidin-3-ol (200 mg, 2.0 mmol) and methylsulfinylmethane (10 mL, 0.2M). The vessel was sealed and the mixture stirred at 90° C. for 24 hrs. Next day the reaction was cooled to RT and diluted with 5 ml of DMSO. The solution was purified by Gilson reverse phase liquid chromatography (10% to 90% CH3CN/H2O/0.1% TFA) to afford 1-(4-chlorophthalazin-1-yl)piperidin-3-ol. MS m/z=264 [M+1]+. Calculated for C13H14ClN3O: 263.7.

Workup

  1. customThe vessel was sealed
  2. temperatureNext day the reaction was cooled to RT
  3. customThe solution was purified by Gilson reverse phase liquid chromatography (10% to 90% CH3CN/H2O/0.1% TFA)

Sources & evidence

ORD record
ord-9a528220d26c4014b3a0888beed932f3
Source dataset
uspto-grants-2009_07
Patent number
US07560551B2

Reaction notes

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