Triethylamine → HCID 70975423, compound

HRID 1190817Notes

Reaction equation

HRID 1190817 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[C:18]([CH3:20])[N:17]=[C:16](Cl)[C:15]=2[N+:22]([O-:24])=[O:23])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:33][O:34][C:35]1[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=[CH:39][C:36]=1[CH2:37][NH2:38].C(OCC)(=O)C>CN1CCCC1=O>[C:1]([O:5][C:6](=[O:25])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[C:18]([CH3:20])[N:17]=[C:16]([NH:38][CH2:37][C:36]3[CH:39]=[CH:40][C:41]([O:43][CH3:44])=[CH:42][C:35]=3[O:34][CH3:33])[C:15]=2[N+:22]([O-:24])=[O:23])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl Acetate2×HCID 5972502,4-DimethoxybenzylamineHCID 86673552HCID 86673552, compound

Product 1

HCID 70975423HCID 70975423, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1.85 g (R)-1-(2-chloro-6-methyl-3-nitropyridin-4-yl)piperidine-3-carbamic acid tert-butyl ester (5 mmol) was dissolved in 10 mL N-methylpyrrolidone, to which 1.4 mL triethylamine (10 mmol) was added, and 1.25 g 2,4-dimethoxybenzylamine (7.5 mmoL) was added. The reaction was continued for 24 h at 80° C. The reaction solution was exacted three times with ethyl acetate. The ethyl acetate phase was combined, washed three times with water, dried, and evaporated to dryness. The resultant crude product was purified through a column chromatography (ethyl acetate:petroleum ether=1:8) to afford 1.83 g titled product with a yield of 73.1%.

Workup

  1. additionwas added
  2. washwashed three times with water
  3. customdried
  4. customevaporated to dryness
  5. customThe resultant crude product was purified through a column chromatography (ethyl acetate:petroleum ether=1:8)

Sources & evidence

ORD record
ord-bc52f337dcd645ceb8bbda0238fab689
Source dataset
uspto-grants-2014_03
Patent number
US08680089B2

Reaction notes

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