Ethyl Acetate → Methyl 2-(2-(piperidin-1-yl)ethylamino)-3-fluorobenzoate

HRID 1695927Notes

Reaction equation

HRID 1695927 reaction equation
F[C:2]1[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[N:13]1([CH2:19][CH2:20][NH2:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.CCOC(C)=O>CN(C=O)C>[N:13]1([CH2:19][CH2:20][NH:21][C:2]2[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 33944N-(2-Aminoethyl)piperidineHCID 2782927Methyl 2,3-difluorobenzoate

Product 1

HCID 57774462Methyl 2-(2-(piperidin-1-yl)ethylamino)-3-fluorobenzoateYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 2,3-difluorobenzoate (0.816 g, 4.741 mmol) and 2-(piperidin-1-yl)ethanamine (2.7 mL, 18.93 mmol) were dissolved in DMF (15 mL) and heated in a microwave for 30 mins at 100° C. The reaction mixture was transferred to a separatory funnel with EtOAc (75 mL) the organics washed with 10 ml pure water. The layers were separated and the aqueous layer was extracted with EtOAc (2×50 mL). The crude material was purified by silica gel column chromatography eluting with EtOAc/Hexanes to give methyl 2-(2-(piperidin-1-yl)ethylamino)-3-fluorobenzoate (837 mg, 63%). LC/MS: 281.17 (M+1) Rt=1.63 min (10-90% 3/5 min (grad/run) with formic acid).

Workup

  1. washthe organics washed with 10 ml pure water
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc (2×50 mL)
  4. customThe crude material was purified by silica gel column chromatography
  5. washeluting with EtOAc/Hexanes

Sources & evidence

ORD record
ord-0fbba02489e94c04858455db722b159f
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

Loading…