4-Fluorobenzoyl chloride → HCID 11337818, compound

HRID 970734Notes

Reaction equation

HRID 970734 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:8])=[O:7])=[CH:4][CH:3]=1.[CH3:11][N:12]([CH3:26])[CH:13]1[CH2:18][CH2:17][C:16]([C:19]2[CH:20]=[C:21]([NH2:25])[CH:22]=[CH:23][CH:24]=2)=[CH:15][CH2:14]1>N1C=CC=CC=1>[ClH:8].[CH3:11][N:12]([CH3:26])[CH:13]1[CH2:18][CH2:17][C:16]([C:19]2[CH:20]=[C:21]([NH:25][C:6](=[O:7])[C:5]3[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=3)[CH:22]=[CH:23][CH:24]=2)=[CH:15][CH2:14]1

Participants

4

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 58852355HCID 58852355, compound

Product 1

HCID 11337818HCID 11337818, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
55 °C

Procedure

Add 4-fluorobenzoyl chloride (155 mg, 0.976 mmol) to a solution of 3-(4-dimethylamino-cyclohex-1-enyl)-phenylamine (preparation 2, 176 mg, 0.814 mmol) in pyridine (8 mL) and heat at 55° C. overnight. Remove the volatile under reduced pressure, dissolve the residue in DCM, wash with 0.1N NaOH, dry over sodium sulfate, filter and concentrate to give a residue. Purify the residue by chromatography (silica gel, 8% 2M NH3/MeOH in DCM) to provide the free base of the title compound (203 mg, 74%): MS (ES): m/z=339.2 (M+H)+; 1H NMR (CDCl3): δ 7.92 (m, 3H), 7.70 (s, 1H), 7.52 (d, 1H), 7.32 (t, 1H), 7.18 (m, 3H), 6.12 (m, 1H), 2.50 (m, 4H), 2.37 (s, 6H), 2.13 (m, 2H), 1.57 (m, 1H).

Workup

  1. customRemove the volatile under reduced pressure
  2. dissolutiondissolve the residue in DCM
  3. washwash with 0.1N NaOH
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customto give a residue
  8. customPurify the residue by chromatography (silica gel, 8% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record
ord-10e72dd64821454fab46066b7fc008bc
Source dataset
uspto-grants-2007_12
Patent number
US07312236B2

Reaction notes

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