Benzoyl chloride → HCID 23353472, compound

HRID 235149Notes

Reaction equation

HRID 235149 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[CH:12]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1>[C:25]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[CH:12]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13]2)=[CH:4][CH:3]=1)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 23353505HCID 23353505, compound2×

Product 1

HCID 23353472HCID 23353472, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-amino-1-(1-methyl-3-pyrrolidinyl)-naphthalene (0.139 g, 0.615 mmol, product of Example 68) and triethylamine (0.103 mL, 0.738 mmol) in tetrahydrofuran (5 mL) was chilled to 0° C. and benzoyl chloride (0.086 mL, 0.738 mmol) was added. The reaction was warmed to room temperature and stirred overnight. The solvent was removed at reduced pressure and the residue was taken up in methylene chloride. The organic layer was washed with 0.5N, sodium hydroxide and brine, dried, concentrated onto silica gel and flash chromatographed (1×2 inches). Elution proceeded as follows: 50% to 75% ethyl acetate/hexane (375 mL), nil; ethyl acetate (200 mL), nil; 2% triethylamine/2% methanol/ethyl acetate (200 mL), 0.14 g of brown oil which partially crystallized. Recrystallization from ethyl acetate gave 0.058 g, (28%) of the title compound as white crystals. mp 137°-145° C.; 1H NMR δ 8.57 (d, J=2 Hz, 1 H), 8.06 (br s, 1 H), 7.95 (dd, J=1.5, 8 Hz, 2 H), 7.86 (d, J=9 Hz, 1 H), 7.71-7.64 (m, 2 H), 7.59-7.49 (m, 4 H), 7.40 (t, J=7.5 Hz, 1 H), 4.15 (sym m, 1 H), 3.04 (t, J=9 Hz, 1 H), 2.93-2.81 (m, 2 H), 2.80-2.68 (m, 1 H), 2.66-2.50 (m, 1 H), 2.47 (s, 3H), 2.08-1.96 (m, 1 H). Analysis calculated for C22H22N20: C, 79.97; H, 6.71; N, 8.48. Found: C, 79.36; H, 6.72; N, 7.94.

Workup

  1. customThe solvent was removed at reduced pressure
  2. washThe organic layer was washed with 0.5N, sodium hydroxide and brine
  3. customdried
  4. concentrationconcentrated onto silica gel and flash
  5. customchromatographed (1×2 inches)
  6. washElution
  7. custom2% triethylamine/2% methanol/ethyl acetate (200 mL), 0.14 g of brown oil which partially crystallized
  8. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-ec41a86877594771a617b8421653f76d
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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