Hydrochloric Acid → 4-(1-(2-allyloxyethyl)-1H-benzimidazole-2-carbonyl)piperidine

HRID 609789Notes

Reaction equation

HRID 609789 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][CH:25]=[CH2:26])[C:19]3[CH:27]=[CH:28][CH:29]=[CH:30][C:18]=3[N:17]=2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[CH2:24]([O:23][CH2:22][CH2:21][N:20]1[C:19]2[CH:27]=[CH:28][CH:29]=[CH:30][C:18]=2[N:17]=[C:16]1[C:14]([CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)=[O:15])[CH:25]=[CH2:26]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 183332581-(t-butoxycarbonyl)-4-(1-(2-allyloxyethyl)-1H-benzimidazole-2-carbonyl)piperidine

Product 1

HCID 183334304-(1-(2-allyloxyethyl)-1H-benzimidazole-2-carbonyl)piperidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Combine 1-(t-butoxycarbonyl)-4-(1-(2-allyloxyethyl)-1H-benzimidazole-2-carbonyl)piperidine (1.0 mmol) and dioxane (3 mL). Add a solution of hydrochloric acid in dioxane (4 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-068429cbcadc47338b67d1de1cf23cf0
Source dataset
uspto-grants-1999_12
Patent number
US05998439

Reaction notes

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