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

HRID 1659263Notes

Reaction equation

HRID 1659263 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 1 N sodium hydroxide is stirred until solution takes place. The pH of the aqueous solution is adjusted to 9 with 6 N 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-677a437821504fd398d2c2e23f00fdf4
Source dataset
uspto-grants-1981_12
Patent number
USRE030812

Reaction notes

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