Triethylamine → HCID 18695630, compound

HRID 1920659Notes

Reaction equation

HRID 1920659 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([NH2:15])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[N:26][CH:25]=1.[OH-].[Na+]>C(Cl)Cl.O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([NH:15][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[N:26][CH:25]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 82604Nicotinoyl chlorideHCID 27793343-(Cyclopentyloxy)-4-methoxyaniline

Product 1

HCID 18695630HCID 18695630, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3.2 g (14.3 mmol) of 3-cyclopentyloxy-4-methoxy-phenylamine (Garcia et al., JOC, 2005, 70, p 1050) were dissolved in 120 ml of DCM. The solution was cooled to 0° C. and 15 ml (107.6 mmol, 7.5 eq.) triethylamine and 3.7 g (26.1 mmol; 1.8 eq) nicotinoyl chloride in 50 ml DCM were added to the reaction mixture. The reaction mixture was stirred for 2 h and then a solution of 1.3 g NaOH in 50 ml water was added to the mixture. The organic phase was separated and washed with water and brine, dried over Na2SO4 and evaporated in vacuo. The crude product was purified by flash chromatography on silica gel (ethyl acetate/n-hexane 1:1) to afford 4 g (85%) of the desired product as a white solid.

Workup

  1. customThe organic phase was separated
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customThe crude product was purified by flash chromatography on silica gel (ethyl acetate/n-hexane 1:1)

Sources & evidence

ORD record
ord-acc72a4540e740669751268e16889d4e
Source dataset
uspto-grants-2012_05
Patent number
US08173609B2

Reaction notes

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