Triethylamine → HCID 66906019, compound

HRID 1689771Notes

Reaction equation

HRID 1689771 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[OH:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(N(CC)CC)C>CN(C=O)C>[CH3:9][O:8][C:6]([C:5]1[CH:10]=[CH:11][C:2]([N:16]2[CH2:17][CH2:18][CH:13]([OH:12])[CH2:14][CH2:15]2)=[N:3][CH:4]=1)=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79341Piperidin-4-olHCID 254249Methyl 6-chloropyridine-3-carboxylate

Product 1

HCID 66906019HCID 66906019, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 6-chloronicotinate (890 mg, 1.00 equiv; 5.03 mmol) in dry DMF (30 mL) is added 4-hydroxypiperidine (1.5 equiv; 7.55 mmol; 778.95 mg) and triethylamine (1.05 mL; 1.5 equiv; 7.55 mmol). The system is flushed with N2 and heated at 80° C. for 4.5 h. The reaction is allowed to reach room temperature and is diluted with water/EtOAc. The aqueous layer is extracted with ethyl acetate (3×). The organic layer is washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude residue is purified via chromatography eluting with hexane/EtOAc 2:1 to 1:2 to yield an orange solid. The solid is triturated with hexane/EtOAc 4:1 and filtered to provide the title compound (1.023 g, 86%) as a white solid. ES/MS m/z 237.0 (M+1)

Workup

  1. customThe system is flushed with N2
  2. customto reach room temperature
  3. additionis diluted with water/EtOAc
  4. extractionThe aqueous layer is extracted with ethyl acetate (3×)
  5. washThe organic layer is washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude residue is purified via chromatography
  10. washeluting with hexane/EtOAc 2:1 to 1:2
  11. customto yield an orange solid
  12. customThe solid is triturated with hexane/EtOAc 4:1
  13. filtrationfiltered

Sources & evidence

ORD record
ord-3a30272c036c4867b45d41ca051aedd3
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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