Hydrochloric Acid → HCID 178478959, compound

HRID 1512169Notes

Reaction equation

HRID 1512169 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4](/[CH:7]=[CH:8]/[C:9]2[NH:13][C:12]3[CH:14]=[CH:15][C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[C:24]([F:27])([F:26])[F:25])=[CH:17][C:11]=3[N:10]=2)[CH2:3][CH2:2]1.[ClH:28].CC(O)C>CCO>[ClH:28].[O:1]1[CH2:6][CH2:5][CH:4](/[CH:7]=[CH:8]/[C:9]2[NH:13][C:12]3[CH:14]=[CH:15][C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[C:24]([F:25])([F:26])[F:27])=[CH:17][C:11]=3[N:10]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 178506129HCID 178506129, compound

Product 1

HCID 178478959HCID 178478959, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (E)-2-[2-(tetrahydro-pyran-4-yl)-vinyl]-5-(2-trifluoromethyl-phenyl)-1H-benzimidazole (0.220 g, 0.591 mmol, prepared as in STEP D above) in EtOH (4 mL) was treated with 5M HCl in i-PrOH (130 μL, 0.650 mmol) at room temperature for 1 h and concentrated in vacuo. The residue was taken up in a minimum amount of EtOH (2 mL). Hexane was added with stirring until the mixture became cloudy. EtOH (1 mL) was added, and hexane was very slowly added until precipitate formed. The resulting mixture was cooled in the refrigerator for 45 min. The solid was filtered, washed with cold hexane, and air-dried to yield (E)-2-[2-(tetrahydro-pyran-4-yl)-vinyl]-5-(2-trifluoromethyl-phenyl)-1H-benzimidazole hydrochloride as an off-white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. additionHexane was added
  3. additionEtOH (1 mL) was added
  4. additionhexane was very slowly added until precipitate
  5. customformed
  6. temperatureThe resulting mixture was cooled in the refrigerator for 45 min
  7. filtrationThe solid was filtered
  8. washwashed with cold hexane
  9. customair-dried

Sources & evidence

ORD record
ord-9684e8adf9184acb8cb76ac735974cbb
Source dataset
uspto-grants-2012_07
Patent number
US08217060B2

Reaction notes

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