Citric Acid → N-{4-[4-(Diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-2-pyridin-3-yl-benzamide citrate salt

HRID 2196190Notes

Reaction equation

HRID 2196190 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].C(Cl)Cl.[C:49]([OH:61])(=[O:60])[CH2:50][C:51]([CH2:56][C:57]([OH:59])=[O:58])([C:53]([OH:55])=[O:54])[OH:52]>C(OCC)(=O)C.C(OCC)C>[C:49]([OH:61])(=[O:60])[CH2:50][C:51]([CH2:56][C:57]([OH:59])=[O:58])([C:53]([OH:55])=[O:54])[OH:52].[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

7

Reactant 4

HCID 311Citric AcidHCID 702EthanolHCID 6344DichloromethaneHCID 25134625Jnj-31020028

Product 1

HCID 25152078N-{4-[4-(Diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-2-pyridin-3-yl-benzamide citrate salt

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 100 mL flask charged with absolute ethanol (25 mL) was added N-{4-[4-(diethylcarbamoyl-phenyl-methyl)-piperazin-1-yl]-3-fluoro-phenyl}-2-pyridin-3-yl-benzamide (495.4 mg, 0.87 mmol). Mild heating with a heat gun, sonication and addition of CH2Cl2 (4 mL) resulted in a homogeneous solution. Citric acid (171.1 mg) was then added in one portion and the resulting mixture was stirred until homogenous, then allowed to stand for 1 h. The solvents were removed with the rotary evaporator to yield an off-white foam. The foam was stirred over a 2:1 mixture of diethyl ether and ethyl acetate (60 mL) for 6 h. The resulting solids were collected on filter paper, washed with diethyl ether and dried under vacuum to yield the title compound as an off-white powder.

Workup

  1. customresulted in a homogeneous solution
  2. customThe solvents were removed with the rotary evaporator
  3. customto yield an off-white foam
  4. customThe resulting solids were collected
  5. filtrationon filter paper
  6. washwashed with diethyl ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-7bc31cd384e54c209c56473b33d1a794
Source dataset
uspto-grants-2012_12
Patent number
US08338426B2

Reaction notes

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