Hydrochloric Acid → 4-({1-[2-(4-cyanophenyl)ethyl]-4-hydroxypiperidin-4-ylmethyl}methylamino)-N-hydroxybenzamide monohydrochloride

HRID 1727099Notes

Reaction equation

HRID 1727099 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][C:14]([CH2:18][N:19]([CH3:36])[C:20]3[CH:35]=[CH:34][C:23]([C:24]([NH:26][O:27]C4CCCCO4)=[O:25])=[CH:22][CH:21]=3)([OH:17])[CH2:13][CH2:12]2)=[CH:5][CH:4]=1)#[N:2].[ClH:37]>CO>[ClH:37].[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][C:14]([CH2:18][N:19]([CH3:36])[C:20]3[CH:21]=[CH:22][C:23]([C:24]([NH:26][OH:27])=[O:25])=[CH:34][CH:35]=3)([OH:17])[CH2:13][CH2:12]2)=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866033454-({1-[2-(4-cyanophenyl)ethyl]-4-hydroxypiperidin-4-ylmethyl}methylamino)-N-(tetrahydropyran-2-yloxy)benzamide

Product 1

HCID 866033464-({1-[2-(4-cyanophenyl)ethyl]-4-hydroxypiperidin-4-ylmethyl}methylamino)-N-hydroxybenzamide monohydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of the compound (0.60 g) obtained in Example 23 in methanol (20 mL) was added 10% hydrogen chloride in methanol (5.0 mL), followed by stirring. The solvent was removed under reduced pressure, the residue was dissolved in methanol, and the solvent was removed again under reduced pressure. The residue was solidified with ethyl acetate, the resulting solid was finely powdered and was collected by filtration. The powder was dissolved in water (60 mL), and the solvent was removed under reduced pressure. The residue was finely powdered and dried under reduced pressure to yield the titled compound (447 mg) as a powder.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in methanol
  3. customthe solvent was removed again under reduced pressure
  4. filtrationwas collected by filtration
  5. dissolutionThe powder was dissolved in water (60 mL)
  6. customthe solvent was removed under reduced pressure
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-2aeaeed88cf94e4481de9abd9f3919ce
Source dataset
uspto-grants-2009_02
Patent number
US07494987B2

Reaction notes

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