4-Fluorobenzoyl chloride → N-(3-(4-Dimethylamino-cyclohex-1-enyl)-2-fluoro-phenyl)-4-fluoro-benzamide hydrochloride salt

HRID 970745Notes

Reaction equation

HRID 970745 reaction equation
[CH3:1][N:2]([CH3:17])[CH:3]1[CH2:8][CH2:7][C:6]([C:9]2[C:10]([F:16])=[C:11]([NH2:15])[CH:12]=[CH:13][CH:14]=2)=[CH:5][CH2:4]1.[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([Cl:25])=[O:24])=[CH:21][CH:20]=1>O1CCOCC1>[ClH:25].[CH3:1][N:2]([CH3:17])[CH:3]1[CH2:8][CH2:7][C:6]([C:9]2[C:10]([F:16])=[C:11]([NH:15][C:23](=[O:24])[C:22]3[CH:26]=[CH:27][C:19]([F:18])=[CH:20][CH:21]=3)[CH:12]=[CH:13][CH:14]=2)=[CH:5][CH2:4]1

Participants

4

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 588523563-(4-Dimethylamino-cyclohex-1-enyl)-2-fluoro-phenylamine

Product 1

HCID 69350852N-(3-(4-Dimethylamino-cyclohex-1-enyl)-2-fluoro-phenyl)-4-fluoro-benzamide hydrochloride saltYield 72%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Reflux a mixture of 3-(4-dimethylamino-cyclohex-1-enyl)-2-fluoro-phenylamine (preparation 8, 0.115 g, 0.49 mmol) and 4-fluoro-benzoyl chloride (93 mg, 0.586 mmol) in dioxane (20 mL) for 2 hrs. Filter the reaction mixture through a SCX column (Bond Elut™, 10 g), wash with MeOH, elute the product with 2M NH3 in MeOH, evaporate the solvent, and further purify on a silica gel column (DCM:2M NH3 in MeOH, gradient) to give the free base of the title compound (0.125 g, 72%): MS (ES): m/z=357 (M+H)+. 1H NMR (CDCl3): δ 8.30 (m, 1H), 8.00 (m, 1H), 7.91 (m, 2H), 7.18 (m, 2H), 7.12 (m, 1H), 6.99 (m, 1H), 5.90 (m, 1H), 2.68 (m, 1H), 2.50 (m, 3H), 2.43 (s, 6H), 2.26 (m, 1H), 2.15 (m, 1H), 1.64 (m, 1H).

Workup

  1. temperatureReflux
  2. filtrationFilter the reaction mixture through a SCX column (Bond Elut™, 10 g)
  3. washwash with MeOH
  4. washelute the product with 2M NH3 in MeOH
  5. customevaporate the solvent
  6. customfurther purify on a silica gel column (DCM:2M NH3 in MeOH, gradient)

Sources & evidence

ORD record
ord-b2ea3b7ecc984a39b093eed72b392f3d
Source dataset
uspto-grants-2007_12
Patent number
US07312236B2

Reaction notes

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