Hydrochloric Acid → HCID 66835687, compound

HRID 572836Notes

Reaction equation

HRID 572836 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([NH:24][CH:25]1[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]1)[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17]C2CCCCO2)[CH:12]=1.Cl.C(=O)([O-])O.[Na+]>C(O)C>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([NH:24][CH:25]1[CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH2:30]1)[C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 66835999HCID 66835999, compound

Product 1

HCID 66835687HCID 66835687, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of {(1H-benzimidazol-2-yl)[3-(tetrahydropyran-2-yloxy)phenyl]methyl}(1-methylpiperidin-4-yl)amine (example 120, 500 mg) in ethanol (5 mL) is treated with aqueous 37% hydrochloric acid at room temperature for one night. The mixture is then neutralized with an aqueous saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by column chromatography (gradient dichloromethane/methanol/ammonia from 90/10/0.5 to 80/20/0.5) to give 3-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-ylamino)methyl]phenol as a white solid melting at 230° C.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe pooled organic extracts are dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by column chromatography (gradient dichloromethane/methanol/ammonia from 90/10/0.5 to 80/20/0.5)

Sources & evidence

ORD record
ord-596254fb2ec24a5ba3d0e7bd821997a1
Source dataset
uspto-grants-2015_05
Patent number
US09029357B2

Reaction notes

Loading…