Ammonia → 4-(1-t-Butoxycarbonylpiperidin-4-yloxy)-3-carbamoyl-5-methylnitrobenzene

HRID 1268219Notes

Reaction equation

HRID 1268219 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([N+:22]([O-:24])=[O:23])=[CH:17][C:16]=2[C:25](O)=[O:26])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OCC(C)C)=O.C([N:38](CC)CC)C.N>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([N+:22]([O-:24])=[O:23])=[CH:17][C:16]=2[C:25](=[O:26])[NH2:38])[CH2:12][CH2:13]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 18542573HCID 18542573, compound

Product 1

HCID 185427554-(1-t-Butoxycarbonylpiperidin-4-yloxy)-3-carbamoyl-5-methylnitrobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(1-t-butoxycarbonylpiperidin-4-yloxy)-3-carboxy-5-methylnitrobenzene (3.6 g) in dichloromethane (60 ml) were added isobutyl chloroformate (1.4 ml) and triethylamine (1.6 ml) in an ice bath and the mixture was stirred at the same temperature for 0.5 hours. To the reaction mixture was added 28% aqueous ammonia (0.7 ml) and the resulting mixture was stirred at room temperature for 1.5 hours. The reaction mixture was concentrated in vacuo. The residue was purified by chromatography on a silica gel column using dichloromethane/methanol=19/1 as an eluant to give the desired compound (3.9 g, yield quantitative) as a yellow oil.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 1.5 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-272ada093d804aeba530c6789241cda6
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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