Methanol → HCID 9820230, compound

HRID 1016432Notes

Reaction equation

HRID 1016432 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][C:17]2[N:21](CCC#N)[C:20]3[CH:26]=[CH:27][CH:28]=[CH:29][C:19]=3[N:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].[C:31](OCC)(=O)[CH3:32].CO>C(O)(C)C.C(=O)(O)[O-].[Na+].C(N(CC)CC)C>[CH2:1]([CH:8]1[CH2:13][CH:12]2[N:11]([CH2:14][CH2:15][CH2:16][C:17]3[NH:21][C:20]4[CH:26]=[CH:27][CH:28]=[CH:29][C:19]=4[N:18]=3)[CH:10]([CH2:31][CH2:32]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 5360545SodiumHCID 18407016HCID 18407016, compound

Product 1

HCID 9820230HCID 9820230, compound

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolvent2×HCID 8471TriethylamineSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 0.4 g of 3-{2-[3-(4-benzyl-piperidin-1-yl)-propyl]-benzoimidazol-1-yl}-propionitrile, 20 mL of isopropanol and 2 mL of 0.4 M sodium in isopropanol was heated to reflux for 2 h. Conversion was complete by TLC (80:20:1 ethyl acetate:methanol:triethylamine). The mixture was cooled, diluted with 10 mL of saturated sodium bicarbonate and concentrated. The residue was partitioned between 3×100 mL of chloroform and 50 mL of water. After drying over magnesium sulfate and concentration under reduced pressure, the residue was purified by preparative TLC eluting with 400:100:25 ethyl acetate:methanol:triethylamine. The major band (UV visualization) was 2-[3-(4-benzyl-piperidin-1-yl)-propyl]-1H-benzimidazole (220 mg): MS (m+1)=334.2; 1H NMR (400 MHz, CDCl3) 7.4 (d, 2H), 7.32 (m, 2H), 7.25 (m, 1H), 7.2 (m, 4H), 3.1 (m, 4H), 2.65 (m, 2H), 2.6 (m, 2H), 2.1 (m, 2H), 2.0 (m, 2H), 1.8 (m, 2H), 1.7 (m, 1H), 1.5 (m, 2H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. customThe residue was partitioned between 3×100 mL of chloroform and 50 mL of water
  6. dry with materialAfter drying over magnesium sulfate and concentration under reduced pressure
  7. customthe residue was purified by preparative TLC
  8. washeluting with 400:100:25 ethyl acetate

Sources & evidence

ORD record
ord-00accbd5e54d4bb1b27e8d3b4b47b56d
Source dataset
uspto-grants-2002_11
Patent number
US06476041B1

Reaction notes

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