1,1'-Carbonyldiimidazole → 1-(3,5-Dimethyl-4-methoxybenzoyl)-4-(3-ethylamino-2-pyridinyl)piperazine

HRID 864431Notes

Reaction equation

HRID 864431 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:13])[C:10]=1[O:11][CH3:12])[C:5]([OH:7])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:26]([NH:28][C:29]1[C:30]([N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)=[N:31][CH:32]=[CH:33][CH:34]=1)[CH3:27].C(=O)(O)[O-].[Na+]>O1CCCC1.ClCCl>[CH3:12][O:11][C:10]1[C:9]([CH3:13])=[CH:8][C:4]([C:5]([N:38]2[CH2:39][CH2:40][N:35]([C:30]3[C:29]([NH:28][CH2:26][CH3:27])=[CH:34][CH:33]=[CH:32][N:31]=3)[CH2:36][CH2:37]2)=[O:7])=[CH:3][C:2]=1[CH3:1]

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 889443,5-Dimethyl-p-anisic acidHCID 516892Sodium BicarbonateHCID 10130476N-Ethyl-2-(piperazin-1-yl)pyridin-3-amine

Product 1

HCID 4553751-(3,5-Dimethyl-4-methoxybenzoyl)-4-(3-ethylamino-2-pyridinyl)piperazine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

3,5-Dimethyl-4-methoxybenzoic acid (I, PREPARATION 3, 0.36 g) is added to a solution of 1,1'-carbonyldiimidazole (0.33 g) in tetrahydrofuran (4 ml) at 20°-25°. After one hour of stirring, 4-[3-(ethylamino)-2-pyridinyl]piperazine (II, International Publication No WO 87/01706 based on International Patent application No PCT/US86/01797, PREPARATION A-47, 0.42 g) in tetrahydrofuran (6 ml) is added and the solution is stirred for 18 hours. The mixture is diluted with dichloromethane and a saturated aqueous sodium bicarbonate solution. The phases are separated, the organic phase is washed with water, then with saline and the phases are separated. The organic phase is dried over sodium sulfate and concentrated under reduced pressure to give an oil. The oil is flash chromatographed on silica gel (230-400 mesh), the product eluted with chloroform, the appropriate fractions are pooled and concentrated to give the title compound.

Workup

  1. additionis added
  2. stirringthe solution is stirred for 18 hours
  3. customThe phases are separated
  4. washthe organic phase is washed with water
  5. customwith saline and the phases are separated
  6. dry with materialThe organic phase is dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give an oil
  9. customchromatographed on silica gel (230-400 mesh)
  10. washthe product eluted with chloroform
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-a70f707ec7784132b7ca4efe04bfb054
Source dataset
uspto-grants-1996_10
Patent number
US05563142

Reaction notes

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