Dimethylamine → HCID 18542638, compound

HRID 1268208Notes

Reaction equation

HRID 1268208 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=2[C:24](O)=[O:25])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OCC(C)C)=O.[CH2:35]([N:37](CC)[CH2:38]C)C.CNC>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=2[C:24](=[O:25])[N:37]([CH3:38])[CH3:35])[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 22181141HCID 22181141, compound

Product 1

HCID 18542638HCID 18542638, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(1-t-butoxycarbonylpiperidin-4-yloxy)-3-carboxynitrobenzene (3.4 g) in dichloromethane (60 ml) were added isobutyl chloroformate (1.4 ml) and triethylamine (1.5 ml) in an ice bath and the mixture was stirred at the same temperature for 0.5 hours. To the reaction mixture was added 50% aqueous dimethylamine (1.1 ml) and the resulting mixture was stirred at room temperature for 2 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 (3.1 g, yield 83%) as a pale yellow amorphous solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 2 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-3d7f5886493543cc93833a1b9831bfb7
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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