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

HRID 379463Notes

Reaction equation

HRID 379463 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.O1CCOCC1.Cl>ClCCl>[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-Dioxane2×HCID 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 6344DichloromethaneSolvent

Procedure

Combine 1-(t-butoxycarbonyl)-4-(1-(2-fur-2-ylmethoxy-ethyl)-1H-benzimidazole-2-carbonyl)piperidine (1.0 mmol) and dioxane (10 mL). Cool in an ice bath. Slowly add a solution of hydrochloric aicd in dioxane (0.25 mL, 4M, 1.0 mmol). After 45 minutes, dilute the reaction mixture with dichloromethane and extract with saturated aqueous sodium bicarbonate solution. Separate the organic layer and extract with brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give the title compound.

Workup

  1. temperatureCool in an ice bath
  2. extractionextract with saturated aqueous sodium bicarbonate solution
  3. customSeparate the organic layer
  4. extractionextract with brine
  5. dry with materialDry the organic layer over Na2SO4
  6. filtrationfilter
  7. customevaporate in vacuo

Sources & evidence

ORD record
ord-211cea3e109241ccbf86aafe073e30f4
Source dataset
uspto-grants-2001_10
Patent number
US06297259B1

Reaction notes

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