HCID 18542735, compound → HCID 18542601, compound

HRID 1268233Notes

Reaction equation

HRID 1268233 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[C:20]([C:21]([O:23]C)=[O:22])=[CH:19][C:18]([N+:25]([O-:27])=[O:26])=[C:17]([CH3:28])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[C:20]([C:21]([OH:23])=[O:22])=[CH:19][C:18]([N+:25]([O-:27])=[O:26])=[C:17]([CH3:28])[CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 18542735HCID 18542735, compound

Product 1

HCID 18542601HCID 18542601, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 4-(1-t-butoxycarbonylpiperidin-4-yloxy)-5-methoxycarbonyl-2-methylnitrobenzene (4.9 g) in concentrated hydrochloric acid (100 ml) was stirred at 80° C. for 5 hours. The reaction mixture was concentrated in vacuo. To a solution of the residual white solid in a mixture of water (30 ml) and acetone (30 ml) were added sodium hydrogencarbonate (2.3 g) and di-t-butyl dicarbonate (3.3 g) at room temperature. The resulting mixture was stirred at 40° C. for 1 hour. The reaction mixture was extracted with ethyl acetate. The extract was washed with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated in vacuo to give the desired compound (4.8 g, yield quantitative) as a yellow amorphous solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionTo a solution of the residual white solid in a mixture of water (30 ml) and acetone (30 ml)
  3. additionwere added sodium hydrogencarbonate (2.3 g) and di-t-butyl dicarbonate (3.3 g) at room temperature
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-ba99b24ab14848c5b2f55e6c15186d5d
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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