Water → HCID 131719030, compound

HRID 22304Notes

Reaction equation

HRID 22304 reaction equation
[ClH:1].[F:2][C:3]([F:31])([F:30])[C:4]1([C:26]([F:29])([F:28])[F:27])[CH:8]([N:9]([CH3:18])[C:10](=[O:17])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[NH:7][C:6]([C:19]2[CH:24]=[CH:23][C:22](F)=[CH:21][CH:20]=2)=[N:5]1.[C:32](=O)([O-])[O-].[K+].[K+].[NH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1.O>CS(C)=O>[ClH:1].[F:2][C:3]([F:30])([F:31])[C:4]1([C:26]([F:29])([F:28])[F:27])[CH:8]([N:9]([CH3:18])[C:10](=[O:17])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[N:7]([CH3:32])[C:6]([C:19]2[CH:20]=[CH:21][C:22]([N:38]3[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)=[CH:23][CH:24]=2)=[N:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 178444174HCID 178444174, compound

Product 1

HCID 131719030HCID 131719030, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of N-[4,4-bis(trifluoromethyl)-2-(4-fluorophenyl)-4,5-dihydro-1H-imidazol-5-yl]-N-methylheptanamide hydrochloride (0.20 g, 0.4 mmole) in dimethyl sulfoxide (5 mL) was added potassium carbonate (0.29 g, 1.2 mmole) and piperidine (0.10 g, 1.2 mmole). The reaction mixture was heated at 145° overnight under nitrogen. The solution was cooled to room temperature, poured into water and extracted with ether. The ether layer was washed with 1N HCL to give unreacted starting material. The aqueous layer was made basic and it was extracted with ether. The organic layer was washed with water and saturated sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under vacuum. The residue was treated with HCl in ether to give the title compound (50 mg, 22%) as a semi solid: MS m/e 521 (M+ +H); 1H NMR (CDCl3 /TMS) δ 0.90(m,3H,CH3), 1.30(m,8H,(CH2)4), 1.67(m,6H,(CH2)3), 2.40(t,2H,CH2), 2.90(s,3H,NCH3), 2.97(s,3H,NCH3), 3.30(m,4H,2CH2), 6.53(s,1H,CH), 6.90(d,2H,Harom), 7.53(d,2H,Harom).

Workup

  1. temperatureThe reaction mixture was heated at 145° overnight under nitrogen
  2. extractionextracted with ether
  3. washThe ether layer was washed with 1N HCL
  4. customto give unreacted
  5. extractionit was extracted with ether
  6. washThe organic layer was washed with water and saturated sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under vacuum
  9. additionThe residue was treated with HCl in ether

Sources & evidence

ORD record
ord-e8f91361543c43bf9de053af0ea7f430
Source dataset
uspto-grants-1995_06
Patent number
US05428041

Reaction notes

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