Hydrochloric Acid → HCID 89690434, compound

HRID 1481884Notes

Reaction equation

HRID 1481884 reaction equation
C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[Cl:12][C:13]1[CH:21]=[C:20](F)[C:19]([N+:23]([O-:25])=[O:24])=[CH:18][C:14]=1[C:15]([OH:17])=[O:16].[F:26][C:27]1[CH:28]=[CH:29][C:30]([CH3:39])=[C:31]([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH:32]=1.Cl>O>[Cl:12][C:13]1[CH:21]=[C:20]([N:36]2[CH2:35][CH2:34][N:33]([C:31]3[CH:32]=[C:27]([F:26])[CH:28]=[CH:29][C:30]=3[CH3:39])[CH2:38][CH2:37]2)[C:19]([N+:23]([O-:25])=[O:24])=[CH:18][C:14]=1[C:15]([OH:17])=[O:16]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 4738810HCID 4738810, compoundHCID 72108282-Chloro-4-fluoro-5-nitrobenzoic Acid

Product 1

HCID 89690434HCID 89690434, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 20 ml scintillation vial equipped with a magnetic stir bar and fitted with a nitrogen inlet, the potassium carbonate (201.60 mg, 1.46 mmol) was suspended in clean, dry N,N-dimethylformamide (2.00 ml, 25.83 mmol) and the 2-chloro-4-fluoro-5-nitro-benzoic acid 1b (160.10 mg, 0.73 mmol) was added to the reaction mixture and stirred until it appeared all the organic solid was taken up into solution. The 1-(5-fluoro-2-methyl-phenyl)-piperazine 16d (170.00 mg, 0.88 mmol) was added to the reaction and the reaction mixture was allowed to stir at room temperature under a nitrogen atmosphere overnight. The reaction mixture was diluted with 10 ml of water and treated with 10 ml of 2N HCl. The product mixture was stirred until no further gas evolved and was then filtered under vacuum. The orange solid that was collected was washed with water and dried under high vacuum. The product, 2-chloro-4-[4-(5-fluoro-2-methyl-phenyl)-piperazin-1-yl]-5-nitro-benzoic acid 16e (222.30 mg, 0.56 mmol), was isolated as a yellow solid and was carried on without further purification. LCMS (m/e)=394 (M+H).

Workup

  1. customIn a 20 ml scintillation vial equipped with a magnetic stir bar
  2. customfitted with a nitrogen inlet
  3. stirringto stir at room temperature under a nitrogen atmosphere overnight
  4. stirringThe product mixture was stirred until no further gas
  5. filtrationwas then filtered under vacuum
  6. customThe orange solid that was collected
  7. washwas washed with water
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-ca84df3633664868a68b59f3f72c96ec
Source dataset
uspto-grants-2016_08
Patent number
US09409897B2

Reaction notes

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