Hydrochloric Acid → 4-Hydroxy-N-{2-[2-(1-methylpiperidin-2-yl)ethyl]phenyl}benzamide

HRID 461902Notes

Reaction equation

HRID 461902 reaction equation
C(O[C:5]1[CH:19]=[CH:18][C:8]([NH:9][C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:7]([CH2:20][CH2:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][N:23]2[CH3:28])[CH:6]=1)(=O)C.Cl.[OH-:30].[Na+]>>[OH:30][C:14]1[CH:15]=[CH:16][C:11]([C:10]([NH:9][C:8]2[CH:18]=[CH:19][CH:5]=[CH:6][C:7]=2[CH2:20][CH2:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][N:23]2[CH3:28])=[O:17])=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20560025HCID 20560025, compound

Product 1

HCID 547364-Hydroxy-N-{2-[2-(1-methylpiperidin-2-yl)ethyl]phenyl}benzamide

Procedure

4'-Acetoxy-2'-[2-(1-methyl-2-piperidyl)-ethyl]benzanilide suspended in 1N sodium hydroxide is stirred until solution takes place. The pH of the aqueous solution is adjusted to 9 with 6N hydrochloric acid and an oil precipitates which is extracted with ethyl acetate. The product isolated by removal of the ethyl acetate solvent is crystallized from ethanol to provide analytically pure 4-hydroxy-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide, m.p. 178.5°-182.5° C. (corr.).

Workup

  1. customan oil precipitates which
  2. extractionis extracted with ethyl acetate
  3. customThe product isolated by removal of the ethyl acetate solvent
  4. customis crystallized from ethanol

Sources & evidence

ORD record
ord-f0c6b3b2f69a43caa1df9eb6c0b51be5
Source dataset
uspto-grants-1977_12
Patent number
US04064254

Reaction notes

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