Benzoyl chloride → 7-Benzoyl-1-(4-methyl-1-piperazinyl)naphthalene

HRID 235133Notes

Reaction equation

HRID 235133 reaction equation
C[Sn](C)(C)[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[CH:5][CH:4]=1.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Cl-].[NH4+]>C(Cl)(Cl)Cl.[Pd](Cl)Cl.C(#N)C.C(#N)C>[C:22]([C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[CH:5][CH:4]=1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 25517Ammonium ChlorideHCID 221156087-Trimethylstannyl-1-(4-methyl-1-piperazinyl)-naphthalene

Product 1

HCID 189675207-Benzoyl-1-(4-methyl-1-piperazinyl)naphthalene

Reagents, catalysts & solvents 2

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalystHCID 6212ChloroformSolvent2×

Procedure

7-Trimethylstannyl-1-(4-methyl-1-piperazinyl)-naphthalene (0.1 g, 0.27 mmol), benzoyl chloride (0.031 mL, 0.27 mmol) and bis (acetonitrile) palladium chloride (0.007 g, 0.027 mmol) were combined in chloroform (5 mL) and heated to 60° to 65° C. for 15 minutes. The reaction was cooled to room temperature and saturated aqueous ammonium chloride (10 mL) and chloroform (10 mL) were added, Phases were separated and the organic layer was washed with brine, dried over magnesium sulfate, and concentrated to a milky oil. The oil was purified by flash chromatography on silica gel (1×6 inches), the product eluting with 5% methanol/ethyl acetate as a yellow oil (0.07 g, 79%). The oil was crystallized from ether to obtain a bright yellow solid: mp 124°-124.5° C. Analysis calculated for C22H22N2O: C, 79.97; H, 6.71; N, 8.48. Found: C, 79.74; H, 6.69; N, 8.46.

Workup

  1. temperatureheated to 60° to 65° C. for 15 minutes
  2. customPhases were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to a milky oil
  6. customThe oil was purified by flash chromatography on silica gel (1×6 inches)
  7. washthe product eluting with 5% methanol/ethyl acetate as a yellow oil (0.07 g, 79%)
  8. customThe oil was crystallized from ether
  9. customto obtain a bright yellow solid

Sources & evidence

ORD record
ord-cb5617be698b485d8f2269933e97cb23
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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