Hydrochloric Acid → HCID 86704021, compound

HRID 1773931Notes

Reaction equation

HRID 1773931 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][CH:9]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][CH2:15][N:14]3[C:10]2=[N:11][C:12]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:13]3[C:23](N)=[O:24])[CH2:4][CH2:3]1.[OH-:32].[Na+].Cl>O>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][CH:9]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][CH2:15][N:14]3[C:10]2=[N:11][C:12]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:13]3[C:23]([OH:24])=[O:32])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86704022HCID 86704022, compound

Product 1

HCID 86704021HCID 86704021, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

To 4-(1-methyl piperidin-4-yloxy)-2-phenyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene-1-carboxylic acid amide (example 254) (250 mg, 0.6 mmole) is added 30% aqueous NaOH solution (2 mL). The reaction mixture is heated to 125° C. overnight. Water (2 mL) is added as well as 1N HCl to pH 6-7. The solvent is removed under reduced pressure. The residue is dissolved in absolute EtOH and filtered to remove inorganic salts. EtOH is removed under reduced pressure. The residue is triturated in Et2O, filtered to afford 4-(1-methylpiperidin-4-yloxy)-2-phenyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene-1-carboxylic acid melting at 185° C.

Workup

  1. customThe solvent is removed under reduced pressure
  2. dissolutionThe residue is dissolved in absolute EtOH
  3. filtrationfiltered
  4. customto remove inorganic salts
  5. customEtOH is removed under reduced pressure
  6. customThe residue is triturated in Et2O
  7. filtrationfiltered

Sources & evidence

ORD record
ord-ac54f3b2b8394a04bb7c8dcc2a4effa8
Source dataset
uspto-grants-2016_02
Patent number
US09255101B2

Reaction notes

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