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

HRID 609786Notes

Reaction equation

HRID 609786 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, 4 M, 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 invacuo 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 invacuo

Sources & evidence

ORD record
ord-30309be5e03348e5a50a60063c03a76a
Source dataset
uspto-grants-1999_12
Patent number
US05998439

Reaction notes

Loading…