Triethylamine → HCID 21701692, compound

HRID 1596224Notes

Reaction equation

HRID 1596224 reaction equation
Br.[N:2]1([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[C:25]([C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1)#[N:26]>ClCCl.C(OCC)(=O)C>[C:25]([C:27]1[CH:35]=[CH:34][C:30]([C:31]([N:5]2[CH2:4][CH2:3][N:2]([NH:8][C:9](=[O:17])[C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)[CH2:7][CH2:6]2)=[O:32])=[CH:29][CH:28]=1)#[N:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 801724-Cyanobenzoyl chlorideHCID 21701628HCID 21701628, compound

Product 1

HCID 21701692HCID 21701692, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of N-piperazinyl-p-fluorobenzamide hydrobromide (300 mg) and triethylamine (0.41 ml) in dichloromethane (6 ml) was added 4-cyanobenzoyl chloride (196 mg) at 0° C. The mixture was stirred at ambient temperature for 3 hours, diluted with ethyl acetate and washed with water (×2). The organic layer was separated, dried over magnesium sulfate, and concentrated. The crystal residue was recrystallized from methanol, ethyl acetate and n-hexane to give N-[4-(4-cyanobenzoyl)-1-piperazinyl]-4-fluorobenzamide (199 mg).

Workup

  1. washwashed with water (×2)
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe crystal residue was recrystallized from methanol, ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-82d9f5fb79ae44a493b8661373676d64
Source dataset
uspto-grants-2001_09
Patent number
US06291464B1

Reaction notes

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