Ammonium Chloride → HCID 71272570, compound

HRID 475105Notes

Reaction equation

HRID 475105 reaction equation
[CH3:1][C:2]1[C:3]([C:17](=[N:19]O)[CH3:18])=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][O:11]3)[C:6]=2[CH:16]=1.[NH4+].[Cl-]>CO.CC(O)=O.[Zn]>[CH3:1][C:2]1[C:3]([CH:17]([NH2:19])[CH3:18])=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][O:11]3)[C:6]=2[CH:16]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86694697HCID 86694697, compound

Product 1

HCID 71272570HCID 71272570, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)ethanone oxime (1.1 g, 4.0 mmol), zinc (2.6 g, 40.0 mmol) and NH4Cl (2.2 g, 40.0 mmol) in MeOH (20 mL) and HOAc (4 mL) was stirred at 80° C. for 4 h. The reaction mixture was filtered and the filtrate concentrated in vacuo. Aqueous ammonia solution (50 mL) was added to the residue, and the mixture was extracted with DCM (50 mL×3), dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH/TEA (10:1:0.2) to afford 1-(6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)ethanamine (101) as a yellow solid (840 mg, 80%). MS (ESI): m/z=260.2 [M+1]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. additionAqueous ammonia solution (50 mL) was added to the residue
  4. extractionthe mixture was extracted with DCM (50 mL×3)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by SiO2 chromatography
  9. washeluting with DCM/MeOH/TEA (10:1:0.2)

Sources & evidence

ORD record
ord-baba59a8ddaa4ab7b4247fe406cd3fd9
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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