Hydrochloric Acid → (2,6-Difluoro-phenyl)-[4-(3-methyl-5-nitro-pyridin-2-yl)-piperazin-1-yl]-methanone

HRID 1993654Notes

Reaction equation

HRID 1993654 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[C:10]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[N:11][CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1.Cl.[F:25][C:26]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:27]=1[C:28](Cl)=[O:29]>C(Cl)Cl>[F:25][C:26]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:27]=1[C:28]([N:21]1[CH2:20][CH2:19][N:18]([C:10]2[C:9]([CH3:8])=[CH:14][C:13]([N+:15]([O-:17])=[O:16])=[CH:12][N:11]=2)[CH2:23][CH2:22]1)=[O:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471Triethylamine2×HCID 874382,6-Difluorobenzoyl chloride2×HCID 566870601-(3-Methyl-5-nitropyridin-2-yl)piperazine

Product 1

HCID 68540471(2,6-Difluoro-phenyl)-[4-(3-methyl-5-nitro-pyridin-2-yl)-piperazin-1-yl]-methanoneYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add triethylamine drop wise (3 equiv) to a suspension of 1-(3-methyl-5-nitro-pyridin-2-yl)-piperazine; hydrochloride (6.91 g, 24.13 mmol) in DCM (120 mL). Add 2,6-difluorobenzoylchloride (1 equiv.) Stir the mixture at room temperature overnight. Add additional 2,6-difluorobenzoylchloride (1.6 mL) and triethylamine (1.5 equiv.) to run reaction to completion. Allow the reaction to stand overnight. Dilute with DCM and extract several times with water. Dry the organic layer over Na2S2O4, filter, and remove solvent under reduced pressure. Wash solid several times with hexane to obtain. 8.08 g of (2,6-difluoro-phenyl)-[4-(3-methyl-5-nitro-pyridin-2-yl)-piperazin-1-yl]-methanone (93% yield). ES+(m/z): 363 [M+1]

Workup

  1. customreaction to completion
  2. customthe reaction
  3. extractionextract several times with water
  4. dry with materialDry the organic layer over Na2S2O4
  5. filtrationfilter
  6. customremove solvent under reduced pressure
  7. washWash solid several times with hexane
  8. customto obtain

Sources & evidence

ORD record
ord-c7c68840d4b44a3c986f10032370b950
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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