Hydrochloric Acid → N-{4-[4-(Diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-2-pyridin-3-yl-benzamide bis-hydrochloride

HRID 2196181Notes

Reaction equation

HRID 2196181 reaction equation
C(O)C.[CH2:4]([N:6]([CH2:44][CH3:45])[C:7]([CH:9]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[N:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:36])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]3[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=3)=[CH:18][C:17]=2[F:37])[CH2:12][CH2:11]1)=[O:8])[CH3:5].[ClH:46]>CCOCC>[ClH:46].[ClH:46].[CH2:44]([N:6]([CH2:4][CH3:5])[C:7]([CH:9]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[N:10]1[CH2:11][CH2:12][N:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:36])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]3[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=3)=[CH:18][C:17]=2[F:37])[CH2:14][CH2:15]1)=[O:8])[CH3:45]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 25134625Jnj-31020028

Product 1

HCID 25152077N-{4-[4-(Diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-2-pyridin-3-yl-benzamide bis-hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 500 mL, round-bottomed flask under a positive pressure of nitrogen was equipped with a magnetic stirrer and charged with absolute ethanol (90 mL) followed by N-{4-[4-(diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-2-pyridin-3-yl-benzamide (4.5 g, 7.9 mmol). 2M HCl in anhydrous ether (7.9 mL, 15.9 mmol) was added drop-wise to the reaction mixture via an addition funnel and the resulting suspension was stirred at ambient temperature for 2 h. The reaction mixture was diluted by the addition of anhydrous ether (90 mL) in a slow stream, which resulted in a gummy solid. The solvents were removed on the rotary evaporator to yield a pale brown foam. The foam was triturated with a mixture of dichloromethane/ether (45 mL each) and the resulting suspension was stirred at ambient temperature for 3 h, then at 0° C. for 1 h. The resulting solid was collected by filtration and the filter-cake was washed with 1:1 dichloromethane/ether (2×40 mL) and dried under house vacuum. The powder was dried further on the rotary evaporator (water bath temperature 50° C.) to yield the title compound as an off-while solid.

Workup

  1. customA 500 mL, round-bottomed flask under a positive pressure of nitrogen was equipped with a magnetic stirrer
  2. customresulted in a gummy solid
  3. customThe solvents were removed on the rotary evaporator
  4. customto yield a pale brown foam
  5. customThe foam was triturated with a mixture of dichloromethane/ether (45 mL each)
  6. stirringthe resulting suspension was stirred at ambient temperature for 3 h
  7. waitat 0° C. for 1 h
  8. filtrationThe resulting solid was collected by filtration
  9. washthe filter-cake was washed with 1:1 dichloromethane/ether (2×40 mL)
  10. customdried under house vacuum
  11. dry with materialThe powder was dried further on the rotary evaporator (water bath temperature 50° C.)

Sources & evidence

ORD record
ord-d6f21bdf841f4039be4b5fd5686e3b04
Source dataset
uspto-grants-2012_12
Patent number
US08338426B2

Reaction notes

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