Triethylamine → 7-(4-Chlorobenzamido)-1-(4-methyl-1-piperazinyl)-naphthalene

HRID 235114Notes

Reaction equation

HRID 235114 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1>C(#N)C>[Cl:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([NH:1][C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][CH:8]=[C:9]3[N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)=[CH:4][CH:3]=2)=[O:32])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 233534847-Amino-1-(4-methyl-1-piperazinyl)-naphthalene

Product 1

HCID 189675117-(4-Chlorobenzamido)-1-(4-methyl-1-piperazinyl)-naphthaleneYield 43.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title product was prepared following the procedure of example 3 from 7-amino-1-(4-methyl-1-piperazinyl)-naphthalene (0.249 g, 1.03 mmol) and triethylamine (0.151 mL, 1.14 mmol) and 4-chlorobenzoyl chloride (0.241 g, 1.14 mmol) in acetonitrile (10 mL) with overnight stirring at room temperature. The product was purified using chromatography and recrystallization from ethyl acetate to yield 0.17 g (43%) of the title compound as a white solid mp 174°-175° C. HRMS m/e calculated for C22H22ClN3O: 379.1448. Observed m/e: 379.1465. Analysis calculated for C22H22ClN3O: C, 69.56; H, 5.84; N, 11.06. Found: C, 69.38; H, 5.80; N, 10.96.

Workup

  1. customThe title product was prepared
  2. customwith overnight
  3. customThe product was purified
  4. customchromatography and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-09bd85beed084074b1d74caac5a4ce9e
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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