Pentylamine → N-[(2'-nitro-1,1'-biphenyl-4-yl)methyl]-N-pentylamine

HRID 492289

Reaction equation

HRID 492289 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6].C(=O)([O-])[O-].[K+].[K+].[N+:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[CH:27]=[CH:26][C:25]([CH2:28]Br)=[CH:24][CH:23]=1)([O-:15])=[O:14].C(OCC)(=O)C>CN(C)C=O>[N+:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][NH:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[CH:24][CH:23]=1)([O-:15])=[O:14]

Participants

6

Reactant 4

HCID 8060PentylamineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 117790721,1'-Biphenyl, 4'-(bromomethyl)-2-nitro-

Product 1

HCID 17860716N-[(2'-nitro-1,1'-biphenyl-4-yl)methyl]-N-pentylamineYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

n-Amylamine (0.54 g) and potassium carbonate (0.98 g) were suspended in dimethylformamide (3.5 mL), and [[2′-nitro-1,1′-biphenyl-4-yl]methyl] bromide (0.51 g) was added in portions. Four hours later, ethyl acetate (20 mL) was added, and the resulting mixture was washed once with water (40 mL) and twice with brine (90 mL, each). The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column (chloroform/ethyl acetate) to afford N-[(2′-nitro-1,1′-biphenyl-4-yl)methyl]-N-pentylamine as a yellow oil (0.40 g). Yield: 77%.

Workup

  1. washthe resulting mixture was washed once with water (40 mL) and twice with brine (90 mL
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2f06d0472f194e309a6ff5cff80b3326
Source dataset
uspto-grants-2009_05
Patent number
US07531576B2

Linked notes

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