2-Chloro-4-fluorobenzoyl chloride → HCID 66938909, compound

HRID 1716923Notes

Reaction equation

HRID 1716923 reaction equation
[F:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][CH:10]1[CH2:15][CH2:14]N(C)CC1.[Cl:17][C:18]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>O1CCOCC1>[Cl:17][C:18]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:19]=1[C:20]([NH:8][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:9][CH:10]2[CH2:15][CH2:14][CH2:2][CH2:3][N:9]2[CH3:10])[C:2]=1[F:1])=[O:21]

Participants

4

Reactant 2

HCID 27365462-Chloro-4-fluorobenzoyl chlorideHCID 58997307HCID 58997307, compound

Product 1

HCID 66938909HCID 66938909, compoundYield 155.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Mix 2-fluoro-N-(1-methyl-piperidin-4-yl)-benzene-1,3-diamine (Preparation 20) (0.08 g) and 2-chloro-4-fluorobenzoyl chloride (83 mg) in 1,4-dioxane (5 mL) and heat at reflux for 2 hr. Partition the reaction mixture between ethyl acetate and saturated aqueous NaCl, dry over anhydrous sodium sulfate, evaporate and purify on a silica gel column (10 g) (dichloromethane-2M NH3 in methanol, gradient) to give 0.106 g of the title compound (78% yield): mass spectrum (ion spray): m/z=380 (M+1); 1H NMR (CDCl3): 8.19 (br s, 1H), 7.83 (dd, 1H), 7.66 (dd, 1H), 7.19 (dd, 1H), 7.09 (ddd, 1H), 7.00 (dd, 1H), 6.52 (ddd, 1H), 3.76 (br d, 1H), 3.29 (m, 1H), 2.81 (br d, 2H), 2.29 (s, 3H), 2.13 (m, 2H), 2.05 (m, 2H), 1.52 (m, 2H).

Workup

  1. temperatureheat
  2. temperatureat reflux for 2 hr
  3. customPartition the reaction mixture between ethyl acetate and saturated aqueous NaCl
  4. dry with materialdry over anhydrous sodium sulfate
  5. customevaporate
  6. custompurify on a silica gel column (10 g) (dichloromethane-2M NH3 in methanol, gradient)

Sources & evidence

ORD record
ord-dd32269e6b844a5d95a852ce976de21c
Source dataset
uspto-grants-2010_09
Patent number
US07803813B2

Reaction notes

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