Methanesulfonic Acid → HCID 72694778, compound

HRID 1773887Notes

Reaction equation

HRID 1773887 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]([CH:15]=[O:16])=[N:4][C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O[CH:24]1[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]1.CS(O)(=O)=O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[N:6]2[C:5]([CH:15]([O:16][CH:24]3[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[CH2:8][CH2:7]2)=[N:4][C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 10340Sodium CarbonateHCID 660484-Piperidinol, 1-methyl-HCID 86703965HCID 86703965, compound

Product 1

HCID 72694778HCID 72694778, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-methyl-1-phenethyl-4-phenyl-imidazole-2-carbaldehyde (example 103B) (50 mg, 0.172 mmole) in CHCl3 (1 mL) is added 4-hydroxy-N-methylpiperidine (198 mg, 1.72 mmoles). Methanesulfonic acid is added dropwise until a purple colour developed. The reaction is completed (TLC control). A saturated solution of Na2CO3 is added to reach pH 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 preparative TLC over silica gel using (CH2Cl2:MeOH:NH4OH) (92.5:7.5:0.75) to give 1-methyl-4-(1-methyl-piperidin-4-yloxy)-2-phenyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene.

Workup

  1. extractionThe aqueous phase is extracted three times with CH2Cl2
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. filtrationfiltered
  4. customthe solvent is removed under reduced pressure
  5. customThe residue is purified by preparative TLC over silica gel using (CH2Cl2:MeOH:NH4OH) (92.5:7.5:0.75)

Sources & evidence

ORD record
ord-d41f64e93ddc4100850c960ef4fa7a55
Source dataset
uspto-grants-2016_02
Patent number
US09255101B2

Reaction notes

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