Isopropanol → HCID 9820230, compound

HRID 2303336Notes

Reaction equation

HRID 2303336 reaction equation
[CH2:1]([CH:8]1[CH2:14][CH:13]2[N:15]([CH2:16][CH2:17][CH2:18][C:19]3[N:23](CCC#N)[C:22]4[CH:28]=[CH:29][CH:30]=[CH:31][C:21]=4[N:20]=3)[CH:10]([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C)C.[Na].C(OCC)(=O)C>C(=O)(O)[O-].[Na+].C(N(CC)CC)C.CO>[CH2:1]([CH:8]1[CH2:9][CH:10]2[N:15]([CH2:16][CH2:17][CH2:18][C:19]3[NH:20][C:21]4[CH:31]=[CH:30][CH:29]=[CH:28][C:22]=4[N:23]=3)[CH:13]([CH2:12][CH2:11]2)[CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 3776IsopropanolHCID 8857Ethyl AcetateHCID 5360545SodiumHCID 18407018HCID 18407018, compound

Product 1

HCID 9820230HCID 9820230, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8471TriethylamineSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 0.4 g of 3-{2-[3-(3-benzyl-8-aza-bicyclo[3.2.1]oct-8-yl)-propyl]-benzimidazol-1-yl }-propionitrile, 20 mL of isopropanol and 2 mL of 0.4M sodium in isopiopanol 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-(3-benzyl-8-aza-bicyclo[3.2.1]oct-8-yl)-propyl]-1H-benzimidazole (258 mg): MS (m+1)=362.5; 1H NMR (400 MHz, CDCl3) 7.58 (d, 1H), 7.52 (d, 1H), 7.6-7.2 (complex, 7H), 3.38 (s, 2H), 3.18 (m, 2H), 2.82 (m, 2H), 2.6 (m, 2H), 2.22 (m, 2H), 2.1 (m, 2H), 1.85 (m, 5H), 1.6 (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-6b0c0a18aff04e7a9d531256a0d9fc16
Source dataset
uspto-grants-2002_08
Patent number
US06432976B1

Reaction notes

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