Methylamine → HCID 18542698, compound

HRID 1268206Notes

Reaction equation

HRID 1268206 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]([OH:26])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OCC(C)C)=O.[CH2:35]([N:37](CC)CC)C.CN>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:26])[NH:37][CH3:35])[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 22181141HCID 22181141, compound

Product 1

HCID 18542698HCID 18542698, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(1-t-butoxycarbonylpiperidin-4-yloxy)-3-carboxynitrobenzene (3.3 g) in dichloromethane (50 ml) were added isobutyl chloroformate (1.4 ml) and triethylamine (1.4 ml) in an ice bath and the mixture was stirred at the same temperature for 0.5 hours. To the reaction mixture was added 40% aqueous methylamine (1.1 ml) and the resulting mixture was stirred at room temperature for 3 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 (3.5 g, yield quantitative) as a yellow amorphous solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 3 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-f93964506ef746989c479529f50ebc93
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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