Methanesulfonic Acid → HCID 72695486, compound

HRID 1773892Notes

Reaction equation

HRID 1773892 reaction equation
CS(O)(=O)=O.[OH:6][CH:7]1[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]1.[CH3:14][C:15]1[N:24]=[C:23]2[N:17]([CH2:18][CH2:19][C:20]3[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=3[CH:22]2O)[C:16]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:14][C:15]1[N:24]=[C:23]2[N:17]([CH2:18][CH2:19][C:20]3[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=3[CH:22]2[O:6][CH:7]2[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]2)[C:16]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 10340Sodium CarbonateHCID 660484-Piperidinol, 1-methyl-HCID 86703968HCID 86703968, compound

Product 1

HCID 72695486HCID 72695486, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of methanesulfonic acid (1.5 mL) and 4-hydroxy-N-methylpiperidine (658 mg, 5.72 mmoles) in CHCl3 (1 mL) cooled at 0° C. is added a solution of 2-methyl-1-phenyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulen-4-ol (example 123B) (166.1 mg, 0.573 mmole) in CHCl3 (2 mL) dropwise. The reaction mixture is allowed to slowly reach room temperature and is stirred at room temperature for 2 hours. The reaction mixture is poured into a solution of saturated Na2CO3 (final pH 9-10). The aqueous phase is extracted three times with CH2Cl2. The organic phase is dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure. The residue is purified by silica gel chromatography using (CH2Cl2:MeOH:NH4OH) with a gradient from (100:0:0) to (95:5:0.5) to give 2-methyl-4-(1-methylpiperidin-4-yloxy)-1-phenyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene.

Workup

  1. customis allowed to slowly reach room temperature
  2. extractionThe aqueous phase is extracted three times with CH2Cl2
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent is removed under reduced pressure
  6. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-8939f910bd3b46c2a444ce842687a1fd
Source dataset
uspto-grants-2016_02
Patent number
US09255101B2

Reaction notes

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