Potassium Carbonate → HCID 9899559, compound

HRID 1859633Notes

Reaction equation

HRID 1859633 reaction equation
[CH3:1][O:2][C:3](=[O:8])[CH2:4][CH2:5][CH2:6]Br.[CH2:9]([CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[CH2:10][CH2:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl.CO>CC#N>[CH3:1][O:2][C:3](=[O:8])[CH2:4][CH2:5][CH2:6][N:16]1[CH2:17][CH2:18][CH:13]([CH2:9][CH2:10][CH2:11][CH3:12])[CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 107604Methyl 4-bromobutyrateHCID 132838674-ButylpiperidineHCID 21226129Dichloromethane methanol

Product 1

HCID 9899559HCID 9899559, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 25 mL reaction flask was added 4-bromo-butyric acid methyl ester (2.04 g, 11.2 mmol), compound 3 (1.51 g, 10.8 mmol) and potassium carbonate (1.63 g, 11.8 mmol) suspended in CH3CN (10 mL). The reaction mixture was stirred over-night at rt followed by filtration and evaporation to dryness. Addition of H2O (50 mL) was followed by extraction with ethyl acetate (3×100 mL). The combined organic phases were dried (MgSO4) and evaporated to dryness, to produce 2.84 g of crude 23. The crude product was subjected to CC [eluent:CH2Cl2:MeOH (99:1)] to give pure 23 (1.93 g, 75%). LC-MS [M+H]+ 241 (cald. 241.2).

Workup

  1. customTo a 25 mL reaction flask
  2. filtrationfollowed by filtration and evaporation to dryness
  3. additionAddition of H2O (50 mL)
  4. extractionwas followed by extraction with ethyl acetate (3×100 mL)
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. customevaporated to dryness
  7. customto produce 2.84 g of crude 23

Sources & evidence

ORD record
ord-7c1578cc8781424eabbd14d6d128e900
Source dataset
uspto-grants-2003_03
Patent number
US06528529B1

Reaction notes

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