Potassium Carbonate → HCID 9899559, compound

HRID 1168859Notes

Reaction equation

HRID 1168859 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(#N)C>[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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 107604Methyl 4-bromobutyrateHCID 132838674-Butylpiperidine

Product 1

HCID 9899559HCID 9899559, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-bromo-butyric acid methyl ester (1.35 g, 7.5 mmol) in dry acetonitrile (10 ml) was added 4-butylpiperidine (1.00 g, 7.1 mmol) and K2CO3 (1.10 g, 7.8 mmol). After stirring at rt for 12 h, the reaction mixture was evaporated to dryness followed by addition of water (15 ml). The aqueous phase was extracted with ethyl acetate (3×20 ml) and the combined organic phases were dried (Na2SO4) and concentrated in vacuo to produce 1.71 g of the crude title compound 76. The crude product was purified by flash chromatography (MeOH:ethyl acetate; 2:8) to give the pure title compound. Yield 1.27 g (74%). 1H NMR (CD3OD): δ3.65 (s, 3H), 2.93 (d, 2H), 2.33 (q, 4H), 1.98 (t, 2H), 1.81 (qv, 2H), 1.69 (d, 2H), 1.35-1.18 (m, 9H), 0.90 (t, 3H).

Workup

  1. customthe reaction mixture was evaporated to dryness
  2. additionfollowed by addition of water (15 ml)
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×20 ml)
  4. dry with materialthe combined organic phases were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto produce 1.71 g of the crude title compound 76
  7. customThe crude product was purified by flash chromatography (MeOH:ethyl acetate; 2:8)

Sources & evidence

ORD record
ord-f700581d329745619bf9e37fa6463513
Source dataset
uspto-grants-2003_09
Patent number
US06627645B2

Reaction notes

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