Hydrochloric Acid → HCID 19876752, compound

HRID 1886021Notes

Reaction equation

HRID 1886021 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][CH2:10][C:11]1[N:15](CC2C=CC=CC=2)[C:14]2[CH:23]=[CH:24][CH:25]=[CH:26][C:13]=2[N:12]=1.Cl.[H][H]>C(O)C.CCOCC.[Pd]=O>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][CH2:10][C:11]1[NH:12][C:13]2[CH:26]=[CH:25][CH:24]=[CH:23][C:14]=2[N:15]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 19876776HCID 19876776, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19876752HCID 19876752, compoundYield 69.1%

Reagents, catalysts & solvents 3

HCID 5083724Palladium monoxideCatalystHCID 702EthanolSolvent3×HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-[3-[(5-bromopentyl)oxy]propyl]-1-(phenylmethyl) benzimidazole (1.7 g) in absolute ethanol (20 ml) containing 1:9 conc. hydrochloric acid:ethanol (3.27 ml) was hydrogenated over pre-reduced 10% palladium oxide on charcoal catalyst (300 mg) in ethanol (5 ml) until the uptake of hydrogen (101 ml) ceased. The mixture was filtered through hyflo and evaporated in vacuo to give an oil, which was dissolved in ether (150 ml) and washed with 8% sodium bicarbonate solution (100 ml), dried and evaporated in vacuo to give an oil. Purification by FCC eluting with hexane-ether (2:3→0:5) gave the title compound as a yellow oil (0.92 g).

Workup

  1. filtrationThe mixture was filtered through hyflo
  2. customevaporated in vacuo
  3. customto give an oil, which
  4. washwashed with 8% sodium bicarbonate solution (100 ml)
  5. customdried
  6. customevaporated in vacuo
  7. customto give an oil
  8. customPurification by FCC
  9. washeluting with hexane-ether (2:3→0:5)

Sources & evidence

ORD record
ord-d9b49651a5df4aceb59f1b0456474e84
Source dataset
uspto-grants-1992_09
Patent number
US05149698

Reaction notes

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