Ammonium Chloride → HCID 71272335, compound

HRID 475110Notes

Reaction equation

HRID 475110 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([C:16](=[N:18]O)[CH3:17])[C:10]=2[N:9]=[CH:8]1.[NH4+].[Cl-]>CO.CC(O)=O.[Zn]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([CH:16]([NH2:18])[CH3:17])[C:10]=2[N:9]=[CH:8]1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86694698HCID 86694698, compound

Product 1

HCID 71272335HCID 71272335, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-4-yl)ethanone oxime (538 mg, 1.02 mmol), Zn (651 mg, 10.2 mmol), and NH4Cl (541 mg, 10.2 mmol) in MeOH (20 mL) and HOAc (5 mL) was stirred at 80° C. for 16 h. The reaction mixture was filtered and the filtrate was concentrated in vacuo. To the residue was added an aqueous NH4OH (50 mL) and the resulting mixture extracted with DCM (50 mL×3). The combined extracts were 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-(1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-4-yl)ethanamine (103) as a yellow solid (458 mg, yield, 90.1%). MS (ESI): m/z=246.1[M+1]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionTo the residue was added an aqueous NH4OH (50 mL)
  4. extractionthe resulting mixture extracted with DCM (50 mL×3)
  5. dry with materialThe combined extracts were dried (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)
  10. customto afford

Sources & evidence

ORD record
ord-5de9d80424224faf828977feb90bb951
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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