Hydrochloric Acid → HCID 66598276, compound

HRID 1038549Notes

Reaction equation

HRID 1038549 reaction equation
C[O:2][C:3]([C:5]1[N:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[C:7]([CH2:24][CH2:25][CH3:26])[CH:6]=1)=[O:4].[OH-].[Na+].Cl>CO>[C:20]([O:19][C:17]([N:14]1[CH2:13][CH2:12][N:11]([C:8]2[C:7]([CH2:24][CH2:25][CH3:26])=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[N:10][CH:9]=2)[CH2:16][CH2:15]1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66598380HCID 66598380, compound

Product 1

HCID 66598276HCID 66598276, compoundYield 124.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-[6-(methoxycarbonyl)-4-propylpyridin-3-yl]piperazine-1-carboxylate (111 mg, 0.307 mmol) in methanol (3.0 mL), 4N aqueous solution of sodium hydroxide (383 μL, 1.53 mmol) was added under ice-cold conditions, and the mixture was stirred at room temperature overnight. The reaction solution was added 4N aqueous solution of hydrochloric acid under ice-cold conditions, and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (chloroform), and the title compound (134 mg (yield >99%)) was obtained as a yellow crystal.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified by silica-gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-723ec12bddb748cbb69507ca79aa1206
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

Loading…