Hydrochloric Acid → HCID 86695325, compound

HRID 2404474Notes

Reaction equation

HRID 2404474 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][CH:9]([C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=2)[C:10]2[NH:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[N:11]=2)[CH2:4][CH2:3]1.[ClH:28]>CO.C(O)(C)C.[Pd]>[ClH:28].[NH:11]1[C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=[C:10]1[CH:9]([O:8][CH:5]1[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]1)[C:19]1[CH:20]=[CH:21][C:22]([NH2:25])=[CH:23][CH:24]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 66836090HCID 66836090, compound

Product 1

HCID 86695325HCID 86695325, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of 2-[(1-methylpiperidin-4-yloxy)(4-nitrophenyl)methyl]-1H-benzimidazole (example 447, 200 mg) in methanol (5 mL) and a solution of 5N hydrochloric acid in isopropanol (0.2 mL) is added 10% palladium on carbon (50 mg). The flask is evacuated and filled with hydrogen (balloon) and stirred overnight at room temperature. The reaction mixture is filtered on celite and the solvents are evaporated under reduced pressure to dryness. The residual solid is triturated twice with diethyl ether and the solid is filtered and dry to afford 4-[(1H-benzimidazol-2-yl)(1-methylpiperidin-4-yloxy)methyl]aniline hydrochloride as a cream-colored solid melting at 185° C.

Workup

  1. customThe flask is evacuated
  2. additionfilled with hydrogen (balloon)
  3. filtrationThe reaction mixture is filtered on celite
  4. customthe solvents are evaporated under reduced pressure to dryness
  5. customThe residual solid is triturated twice with diethyl ether
  6. filtrationthe solid is filtered
  7. customdry

Sources & evidence

ORD record
ord-e39ddab74f954575a94494248257e2c0
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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