Hydrochloric Acid → HCID 19379079, compound

HRID 2210557Notes

Reaction equation

HRID 2210557 reaction equation
C(O[C:4](=[O:29])[C:5](=[O:28])[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[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:13]=2)[CH2:8][CH2:7]1)C.[NH2:30][OH:31].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:28])[C:4]([NH:30][OH:31])=[O:29])[CH2:7][CH2:8]3)[CH:17]=[CH:16][C:15]=2[O:18][CH3:19])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 23689386Potassium hydroxide methanolHCID 54066446HCID 54066446, compound

Product 1

HCID 19379079HCID 19379079, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-[4-(3-cycloheptylidenemethyl-4-methoxy-phenyl)-piperidin-1-yl]-oxo-acetic acid ethyl ester (0.6 mmol, 0.250 g) in methanol (5 mL) was added hydroxylamine.HCl (2.4 mmol, 0.167 g, followed by KOH/MeOH solution (5M, 600 μL) dropwise at room temperature. A white solid precipitated out of solution at this reaction continued to stir overnight at room temperature. The reaction went to completion as seen by TLC. The reaction mixture was diluted with H2O (150 mL), acidified with 1N HCl and then extracted with EtOAc (3×100 mL). Each organic phase was washed with H2O (1×100 mL) and the combined organics were dried (Na2SO4) and concentrated to yield a white solid. The solid was triturated in Et2O/hexane to afford the pure title compound, mp 135°-136° C. (0.3 mmol, 0.125 g, 54%).

Workup

  1. customA white solid precipitated out of solution at this reaction
  2. additionThe reaction mixture was diluted with H2O (150 mL)
  3. extractionextracted with EtOAc (3×100 mL)
  4. washEach organic phase was washed with H2O (1×100 mL)
  5. dry with materialthe combined organics were dried (Na2SO4)
  6. concentrationconcentrated
  7. customto yield a white solid
  8. customThe solid was triturated in Et2O/hexane

Sources & evidence

ORD record
ord-22dbc5b5f2574e809ad2f6d0b68ed7b4
Source dataset
uspto-grants-1995_10
Patent number
US05459151

Reaction notes

Loading…