Triethylamine → HCID 23353501, compound

HRID 235111Notes

Reaction equation

HRID 235111 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]([CH2:18]O)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[N+:27]([C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33](Cl)=[O:34])([O-:29])=[O:28]>C(#N)C>[N+:27]([C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[N:12]2[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]2)=[CH:4][CH:3]=1)=[O:34])([O-:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8495Benzoyl chloride, 3-nitro-HCID 23353539HCID 23353539, compound

Product 1

HCID 23353501HCID 23353501, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title product was prepared following the procedure of example 3 from 7- amino-1-(4-methylol-piperazinyl)-naphthalene (0.15 g, 0.622 mmol) and triethylamine (0.09 mL, 0.68 mmol) and 3-nitrobenzoyl chloride (0.127 mL, 0.684 mmol) in acetonitrile (10 mL) with an overnight reflux. The product was purified by silica gel flash chromatography followed by recrystallization from ethyl acetate to yield 0.116 g (47%) of the title product: mp 182°-184° C. Analysis calculated for C22H22N4O3 : C, 67.68; H, 5.68; N, 14.35. Found: C, 67.47; H, 5.64; N, 14.08.

Workup

  1. customThe title product was prepared
  2. customwith an overnight
  3. temperaturereflux
  4. customThe product was purified by silica gel flash chromatography
  5. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-9eb37aa1c79343239a189b6a62a3d59e
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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