Hydrochloric Acid → HCID 59809549, compound

HRID 2114498Notes

Reaction equation

HRID 2114498 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH:21]3[CH2:26][CH2:25][N:24]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:23][CH2:22]3)[C:10]3[C:15]([O:16][C:17]=2[CH:18]=1)=[C:14]([O:19][CH3:20])[CH:13]=[CH:12][CH:11]=3)=[O:4].[OH-].[Na+].O.Cl>O1CCOCC1>[CH2:27]([N:24]1[CH2:23][CH2:22][CH:21]([N:9]2[C:8]3[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:18][C:17]=3[O:16][C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][C:14]=3[O:19][CH3:20])[CH2:26][CH2:25]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 59809540HCID 59809540, compound2×

Product 1

HCID 59809549HCID 59809549, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 10-(1-benzyl-piperidin-4-yl)-6-methoxy-10H-phenoxazine-3-carboxylic acid methyl ester, 2d (270 mg, 0.7 mmol) in dioxane (15 mL) was added sodium hydroxide (31 mg, 0.77 mmol) and the mixture was heated to reflux for 4 h. The mixture was allowed to cool to rt, water (15 mL) was added, and the solution was acidified with 1N HCl to pH 2. The mixture was extracted with methylene chloride, the organic phase was separated, dried, and evaporated to yield 245 mg (94%) of title compound 10-(1-benzyl-piperidin-4-yl)-6-methoxy-10H-phenoxazine-3-carboxylic acid, 3d.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 h
  3. extractionThe mixture was extracted with methylene chloride
  4. customthe organic phase was separated
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-628078eae7274aa78145a854f995e836
Source dataset
uspto-grants-2008_10
Patent number
US07432257B2

Reaction notes

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