Triethylamine → 7-(3-Chlorobenzamido)-1-(4-methyl-1-piperazinyl)-naphthalene

HRID 235112Notes

Reaction equation

HRID 235112 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:28]=[C:29]([CH:33]=[CH:34][CH:35]=1)[C:30](Cl)=[O:31]>C(#N)C>[Cl:26][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=1)[C:30]([NH: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)=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69252Benzoyl chloride, 3-chloro-HCID 233534847-Amino-1-(4-methyl-1-piperazinyl)-naphthalene

Product 1

HCID 233534867-(3-Chlorobenzamido)-1-(4-methyl-1-piperazinyl)-naphthaleneYield 20.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title product was prepared following the procedure of example 3 from 7-amino-1-(4-methyl-l-piperazinyl)-naphthalene (0.24 g, 0.995 mmol) and triethylamine (0.146 mL, 1.09 mmol) and 3-chlorobenzoyl chloride (0.138 mL, 1.09 mmol) in acetonitrile (10 mL) with overnight stirring at room temperature. The product was isolated using flash chromatography and trituration from hexane and recrystallization from ethyl acetate (with a seed crystal) to yield 0.076g (20%) of the title compound: mp 147°-148° C. HRMS m/e calculated for C22H22ClN3O; 379.1448. Observed m/e: 379.14473. Analysis calculated for C22H22ClN3O: C, 69.56; H, 5.84; N, 11.06. Found: C, 68.95; H, 5.81; N, 10.96.

Workup

  1. customThe title product was prepared
  2. customwith overnight
  3. customThe product was isolated
  4. customfrom hexane and recrystallization from ethyl acetate (with a seed crystal)

Sources & evidence

ORD record
ord-7d208e85ae624e5e8e436a592944a687
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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