Sodium hydride → 5-[3(Cyclopentyloxy)-4-methoxyphenyl]-1-methyl-2-[3-(3-pyridinyl)propyl]-3-pyrazolidinone

HRID 1655630Notes

Reaction equation

HRID 1655630 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[N:19]([CH3:20])[NH:18][C:17](=[O:21])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:25][CH2:26][CH2:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1>CN(C)C=O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[N:19]([CH3:20])[N:18]([CH2:25][CH2:26][CH2:27][C:28]4[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=4)[C:17](=[O:21])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 127015683-(3-Bromopropyl)pyridineHCID 197927655-[3-(Cyclopentyloxy)-4-methoxyphenyl]-1-methyl-3-pyrazolidinone

Product 1

HCID 197927745-[3(Cyclopentyloxy)-4-methoxyphenyl]-1-methyl-2-[3-(3-pyridinyl)propyl]-3-pyrazolidinoneYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 5-[3-(cyclopentyloxy)-4-methoxy-phenyl]-1-methyl-3-pyrazolidinone (1.10 gms, 3.79 mmol), NaH (0.15 gms, 60%, 3.75 mmol), and dimethylformamide (15 mls) is added a solution of 1-bromo-3-(3-pyridinyl)propane [see Mioque, M., and Gautier, J. A. (1961). C. R. Hebd. Seances Acad. Sci. 252, 2416.] (1.66 gms, 8.30 mmol) in dimethylformamide (5 mls). The reaction is immersed in an oil bath (65° C.). After 20 hours dimethylformamide is removed in vacuo , the residue is diluted in methylene chloride, washed with saturated aqueous NaHCO3 and dried over Na2SO4 - The product was concentrated and chromatographed (SiO2 : 1) 1:1 ethyl acetate:hexane; 2) 2:1 ethyl acetate:hexane; 3) ethyl acetate; 4) 3% methanol:ethyl acetate) to yield 0.85 gms (52%) of an oil. 1H NMR (DMSO-d6, 400 MHz) δ 8.40 (m,2H), 7.55 (m,1H), 7.25 (m,1H), 6.95 (s,1H), 6.85 (m,1H), 5.75 (s,0.5H) 4.70 (m,1H), 4.00 (m,1H), 3.70 (s,3H), 3.60 (m,1H), 3.10 (m,1H), 2.55 (s,3H), 2.45 (m,4H) 1.75 (m,4H), 1.65 (m,4H), 1.50 (m,2H). IR(KBR, cm-) 1685 (C=O).

Workup

  1. customThe reaction is immersed in an oil bath
  2. custom(65° C.)
  3. customAfter 20 hours dimethylformamide is removed in vacuo
  4. additionthe residue is diluted in methylene chloride
  5. washwashed with saturated aqueous NaHCO3
  6. dry with materialdried over Na2SO4 - The product
  7. concentrationwas concentrated
  8. customchromatographed (SiO2 : 1) 1:1 ethyl acetate

Sources & evidence

ORD record
ord-6b69dc35b6a94326bc80f459407b21f3
Source dataset
uspto-grants-1993_10
Patent number
US05250700

Reaction notes

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