Methanol → Acridine

HRID 1421097Notes

Reaction equation

HRID 1421097 reaction equation
C(N(CC)CC)C.Cl.Cl.NCCCCCCN[C:18]1[C:19]2[C:24]([N:25]=[C:26]3[C:31]=1[CH:30]=[CH:29][CH:28]=[CH:27]3)=[CH:23][CH:22]=[CH:21][CH:20]=2.CO>C(Cl)(Cl)Cl>[CH:20]1[C:19]2[C:24](=[N:25][C:26]3[C:31]([CH:18]=2)=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 11245515HCID 11245515, compound

Product 1

HCID 9215Acridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 76 mg (0.168 mmol) of TFP ester 4 in 3 mL of chloroform was added 94 μL of triethylamine (0.67 mmol). 1.23 ml of a 50 mg/mL solution of 9-(6-aminohexylamino)acridine dihydrochloride in methanol (61.5 mg, 0.168 mmol) was added to the stirred solution. HPLC analysis after 1 hour showed complete reaction of the starting TFP ester. The reaction mixture was partitioned between 15 mL of methylene chloride and 10 mL of water. The organic phase was washed with 10 mL of water, dried over sodium sulfate, and concentrated in vacuo. The residue was chromatographed on silica gel and the desired product was eluted with a gradient of 90:5:5-methylene chloride: triethylamine:methanol in hexanes. Removal of solvents gave the desired product 5 as a red solid: TLC (90:5:5-methylene chloride: triethylamine:methanol) Rf =0.79; 1H NMR (CDCl3) δ 8.12 (d, 2H, J=8.8 Hz,), 8.07 (d, 2H, J=8.8 Hz), 7.68 (t, 2H, J=6.9 Hz), 7.37 (t, 2H, J=7.4 Hz), 5.60 (s, 1H), 5.2 (br s, 1H), 3.82 (t, 2H, J=7.1 Hz), 3.21 (q, 2H, J=6.6 Hz), 2.54 (m, 2H), 2.2 (m, 10H), 1.98 (s, 3 H), 1.8-1.65 (m, 6H), 1.5-1.3 (m, 6H).

Workup

  1. customThe reaction mixture was partitioned between 15 mL of methylene chloride and 10 mL of water
  2. washThe organic phase was washed with 10 mL of water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel
  6. washthe desired product was eluted with a gradient of 90:5
  7. customRemoval of solvents

Sources & evidence

ORD record
ord-49079ca3315848a79ae27badfa042792
Source dataset
uspto-grants-2000_06
Patent number
US06072046

Reaction notes

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