Hydrochloric Acid → 4-(1-(2-(fur-2-ylmethoxy)ethyl)-1H-benzimidazole-2-carbonyl)piperidine

HRID 2269872Notes

Reaction equation

HRID 2269872 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:16]2[N:20]([CH2:21][CH2:22][O:23][CH2:24][C:25]3[O:26][CH:27]=[CH:28][CH:29]=3)[C:19]3[CH:30]=[CH:31][CH:32]=[CH:33][C:18]=3[N:17]=2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[O:26]1[CH:27]=[CH:28][CH:29]=[C:25]1[CH2:24][O:23][CH2:22][CH2:21][N:20]1[C:19]2[CH:30]=[CH:31][CH:32]=[CH:33][C:18]=2[N:17]=[C:16]1[C:14]([CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 183334651-(t-Butoxycarbonyl)-4-(1-(2-fur-2-ylmethoxy-ethyl)-1h-benzimidazole-2-carbonyl)piperidine

Product 1

HCID 183335034-(1-(2-(fur-2-ylmethoxy)ethyl)-1H-benzimidazole-2-carbonyl)piperidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Combine 1-(t-butoxycarbonyl)-4-(1-(2-fur-2-ylmethoxy-ethyl)-1 H-benzoimidazole-2-carbonyl)-piperidine (0.43 g, 0.94 mmol) and dioxane (3 mL). Add a solution of hydrochloric acid in dioxane (4.0 mL, 4 M, 16 mmol). After 30 minutes, partition the residue between ethyl acetate and saturated aqueous sodium bicarbonate solution. Separate the organic layer and extract with saturated aqueous sodium chloride solution. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give the title compound.

Workup

  1. custompartition the residue between ethyl acetate and saturated aqueous sodium bicarbonate solution
  2. customSeparate the organic layer
  3. extractionextract with saturated aqueous sodium chloride solution
  4. dry with materialDry the organic layer over Na2SO4
  5. filtrationfilter
  6. customevaporate in vacuo

Sources & evidence

ORD record
ord-0e8324f52f834b169d6bc1d9d516a8ac
Source dataset
uspto-grants-2001_12
Patent number
US06329392B1

Reaction notes

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