tert-butyl N-(4-aminobutyl)carbamate → Tert-butyl 4-(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)butylcarbamate

HRID 1070778Notes

Reaction equation

HRID 1070778 reaction equation
N[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)[C:18]([CH3:25])=[C:17]([CH3:26])[N:16]=1.CN(C)C=O.C(N(CC)CC)C>C(OCC)(=O)C>[Cl:14][C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[C:19]([CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[C:18]([CH3:25])=[C:17]([CH3:26])[N:16]=1

Participants

6

Reactant 4

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 6228DimethylformamideHCID 8471TriethylamineHCID 121091232,4-Dichloro-5,6-dimethyl-3-nitropyridine

Product 1

HCID 21973830Tert-butyl 4-(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)butylcarbamateYield 79.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Tert-butyl 4-aminobutylcarbamate (60 g, 339 mmol) was slowly added to a mixture of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (50 g, 226 mmol), anhydrous N,N-dimethylformamide (500 mL) and triethylamine (50 mL, 339 mmol). The reaction mixture was allowed to stir overnight and then it was concentrated under reduced pressure to provide an oil. The oil was dissolved in ethyl acetate and then washed with water. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure to provide a dark oil. This material was purified by column chromatography (silica gel eluting with 40/60 ethyl acetate/hexanes) to provide 64.5 g of tert-butyl 4-(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)butylcarbamate as a bright orange oil which solidified on standing.

Workup

  1. concentrationit was concentrated under reduced pressure
  2. customto provide an oil
  3. washwashed with water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto provide a dark oil
  7. customThis material was purified by column chromatography (silica gel eluting with 40/60 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-e09bfa8abdff4282ad5b79e2e340d8c1
Source dataset
uspto-grants-2005_06
Patent number
US06903113B2

Reaction notes

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