Hydrochloric Acid → HCID 19379084, compound

HRID 2210555Notes

Reaction equation

HRID 2210555 reaction equation
C([O:3][C:4](=O)[C:5](=[O:26])[N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([CH:20]=[C:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:13]=2)[CH2:8][CH2:7]1)C.[NH2:28][OH:29].Cl.[OH-].[K+].CO>CO>[C:21]1(=[CH:20][C:14]2[CH:13]=[C:12]([CH:9]3[CH2:10][CH2:11][N:6]([C:5](=[O:26])[C:4]([NH:28][OH:29])=[O:3])[CH2:7][CH2:8]3)[CH:17]=[CH:16][C:15]=2[O:18][CH3:19])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 23689386Potassium hydroxide methanolHCID 54548771HCID 54548771, compound

Product 1

HCID 19379084HCID 19379084, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-[4-(3-cyclopentylidenemethyl-4-methoxy-phenyl)-piperidin-1-yl]-oxo-acetic acid ethyl ester (0.4 mmol, 0.150 g) in methanol (5 mL) was added hydroxylamine.HCl (1.6 mmol, 0.111 g), followed by potassium hydroxide/methanol solution (5 M solution; 0.4 mL) dropwise at room temperature. A white solid precipitated out of solution as this reaction stirred for 3 hours. The reaction went to completion as seen by TLC. The reaction mixture was diluted with H2O (100 mL), acidified with 1N HCl and extracted with EtOAc (3×100 mL). Each organic phase was washed with H2O (1×50 mL) and the combined organics were dried (Na2SO4) and concentrated in vacuo to a white solid. The solid was triturated in Et2O/hexane to afford pure white crystals which were dried overnight at 45° C. to give the title compound, mp 127°-128° C. (0.3 mmol, 0.017 g, 75%).

Workup

  1. customA white solid precipitated out of solution as this reaction
  2. additionThe reaction mixture was diluted with H2O (100 mL)
  3. extractionextracted with EtOAc (3×100 mL)
  4. washEach organic phase was washed with H2O (1×50 mL)
  5. dry with materialthe combined organics were dried (Na2SO4)
  6. concentrationconcentrated in vacuo to a white solid
  7. customThe solid was triturated in Et2O/hexane
  8. customto afford pure white crystals which
  9. customwere dried overnight at 45° C.

Sources & evidence

ORD record
ord-5435d0e535bb42c7bee8a7d0f09ecbfa
Source dataset
uspto-grants-1995_10
Patent number
US05459151

Reaction notes

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