tert-butyl N-(4-aminobutyl)carbamate → Tert-butyl 4-[(2-chloro-6-methyl-3-nitropyridin-4-yl)amino]butylcarbamate

HRID 11350

Reaction equation

HRID 11350 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[Cl:14][C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[C:19](Cl)[CH:18]=[C:17]([CH3:25])[N:16]=1>CN(C)C=O>[Cl:14][C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[C:19]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH:18]=[C:17]([CH3:25])[N:16]=1

Participants

4

Reactant 2

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 27848192,4-Dichloro-6-methyl-3-nitropyridine

Product 1

HCID 12109135Tert-butyl 4-[(2-chloro-6-methyl-3-nitropyridin-4-yl)amino]butylcarbamateYield 98.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of tert-butyl 4-aminobutylcarbamate (32.12 g, 170.6 mmol) in N,N-dimethylformamide (200 mL) was added over a period of 90 minutes to a solution of 2,4-dichloro-6-methyl-3-nitropyridine (35.09 g, 169.5 mmol) in N,N-dimethylformamide (500 mL). The reaction mixture was stirred at ambient temperature overnight. The solvent was removed by vacuum distillation using a 24/40 short path distillation head and warm water. The residue was dissolved in ethyl acetate (700 mL), washed with water (3×100 mL), dried over magnesium sulfate and then concentrated under reduced pressure. The crude product was purified by column chromatography (50×450 mm silica gel eluting with 1:1 hexane:ethyl acetate) to provide 59.90 g of tert-butyl 4-[(2-chloro-6-methyl-3-nitropyridin-4-yl)amino]butylcarbamate.

Workup

  1. customThe solvent was removed by vacuum distillation
  2. distillationa 24/40 short path distillation head
  3. temperaturewarm water
  4. dissolutionThe residue was dissolved in ethyl acetate (700 mL)
  5. washwashed with water (3×100 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by column chromatography (50×450 mm silica gel eluting with 1:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-fded4986a54d42f184599c02d1ee8017
Source dataset
uspto-grants-2006_08
Patent number
US07098221B2

Linked notes

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