Hydrochloric Acid → 4-(1H-Benzoimidazol-2-YL)-1,4-diaza-bicyclo[3,2.2]nonane

HRID 1815764Notes

Reaction equation

HRID 1815764 reaction equation
Cl.C(OC([N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[N:18]1[CH:24]2[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]2)[CH2:20][CH2:19]1)=O)(C)(C)C>>[NH:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[N:18]1[CH:24]2[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]2)[CH2:20][CH2:19]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 691520292-(1,4-Diaza-bicyclo[3.2.2]non-4-yl)-benzoimidazole-1-carboxylic acid tert-butyl ester

Product 1

HCID 224957844-(1H-Benzoimidazol-2-YL)-1,4-diaza-bicyclo[3,2.2]nonaneYield 68%

Procedure

1 N Hydrochloric acid (3 mL, in methanol) was added to of 2-(1,4-diaza-bicyclo[3.2.2]non-4-yl)-benzoimidazole-1-carboxylic acid tert-butyl ester (104 mg, 0.304 mmol). The mixture was stirred at RT for 18 h and concentrated. The residue was diluted with 1 N hydrochloric acid (3 mL, aq.) and extracted with ethyl acetate (3×). The aqueous layer was treated with 6 N sodium hydroxide (3 mL, aq.) and extracted with chloroform (6×). The combined organic layers were dried (Na2SO4), filtered and concentrated to afford 50 mg (68%) of the title compound: 1H NMR (CD3OD, 400 MHz) δ 7.19 (dd, 2H, J=5.8 Hz, 3.3 Hz), 6.95 (dd, 2H, J=5.8, 2.9 Hz), 4.98 (br s, 1H), 4.27-4.24 (m, 1H), 3.83 (t, 2H, J=5.8 Hz), 3.09-2.91 (m, 6H), 2.16-2.08 (m, 2H), 1.87-1.78 (m, 2H); MS (Cl) m/z 243.3 (M+1). The hydrochloride salt was prepared by diluting in ethyl acetate and adding a 2.5 N HCl solution in ethyl acetate: mp>300° C.

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with 1 N hydrochloric acid (3 mL, aq.)
  3. extractionextracted with ethyl acetate (3×)
  4. additionThe aqueous layer was treated with 6 N sodium hydroxide (3 mL, aq.)
  5. extractionextracted with chloroform (6×)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7147cfef22a744e98de111b8bb88dc34
Source dataset
uspto-grants-2005_04
Patent number
US06881734B2

Reaction notes

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