Hydrochloric Acid → 4-(2,3-Dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidineacetic acid

HRID 1611430Notes

Reaction equation

HRID 1611430 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]([O:16]CC)=[O:15])[CH2:9][CH2:8]2)[C:5]2[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=2[NH:3]1.[OH-].[Na+].Cl>CO>[O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]([OH:16])=[O:15])[CH2:9][CH2:8]2)[C:5]2[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=2[NH:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20750053HCID 20750053, compound

Product 1

HCID 220370584-(2,3-Dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidineacetic acidYield 146%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl (4-(2-keto-1-benzimidazolinyl)piperidin-1-yl)acetate (13.0 g, 42.8 mmol) in methanol (150 mL) was treated with an aqueous solution of sodium hydroxide (3 N, 30 mL, 90 mmol) and heated at reflux for 2 hours. The solution was cooled to room temperature and neutralized with the addition of concentrated hydrochloric acid (12 N, 7.5 mL). The solvent was evaporated in vacuo, and the resultant amorphous solid was dried in vacuo with heating (˜50° C.) overnight to give (4-(2-keto-1-benzimidazolinyl)piperidin-1-yl)acetic acid (17.2 g) which was used in the subsequent step without purification. MS m/z 304 (MH+); NMR(DMSO-d6): δ 1.74 (br d, 2 H), 2.53-2.67 (m, 2 H), 2.74-2.86 (m, 2 H), 3.33 (s, 2 H), 4.29-4.42 (m, 1 H), 6.97-7.05 (m, 3 H) and 7.38-7.43 (m, 1 H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. customThe solvent was evaporated in vacuo
  4. customwas dried in vacuo
  5. temperaturewith heating (˜50° C.) overnight

Sources & evidence

ORD record
ord-d5f616c088284d209d3e577b039df661
Source dataset
uspto-grants-2006_01
Patent number
US06987188B2

Reaction notes

Loading…