1-Naphthoic acid → HCID 18933042, compound

HRID 1598481Notes

Reaction equation

HRID 1598481 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:8]1([C:18](O)=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>>[C:8]1([C:18]([N:1]2[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 4

HCID 68471-Naphthoic acidHCID 68163Hexahydro-1,4-diazepineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 18933042HCID 18933042, compound

Procedure

Homopiperazine (0.60 g, 6.0 mmol), naphthalene carboxylic acid (0.51 g, 3.0 mmol), 1-hydroxybenzotriazole (0.45 g, 3 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC.HCl) (0.63 g, 3.3 mmol) were added to dry, degassed dimethylformamide (7 mL). The pH of the reaction was adjusted to 7 with triethylamine, and the reaction stirred overnight. The dimethylformamide was distilled in vacuo, and the residue partitioned between ethyl acetate and water. The organic phase was washed with water and saturated sodium chloride solution, and dried over magnesium sulfate. The crude product was chromatographed on silica gel using chloroform/methanol as eluant and the title compound was isolated (0.100 g). NMR (CDCl3, 300 MHz) d 7.88 (2H, m), 7.50 (3H, m), 7.27 (1H, m), 4.08 (1H, m), 3.81 (1H, m), 3.28 (2H, m), 3.18 (1H, m), 3.00 (1H, m), 2.92 (1H, t, J=7 Hz), 2.72 (1H, t, J=7 Hz), 2.20 (1H, m), 1.58 (1H, m).

Workup

  1. customto dry
  2. customdegassed dimethylformamide (7 mL)
  3. distillationThe dimethylformamide was distilled in vacuo
  4. customthe residue partitioned between ethyl acetate and water
  5. washThe organic phase was washed with water and saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThe crude product was chromatographed on silica gel

Sources & evidence

ORD record
ord-a7f0a1ee815d474189b2e07485e9be96
Source dataset
uspto-grants-1998_04
Patent number
US05736539

Reaction notes

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