Hydrochloric Acid → [1-(4-Methoxycarbonylphenyl)cyclopropyl]azanium chloride

HRID 870065Notes

Reaction equation

HRID 870065 reaction equation
[Cl-:1].[C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2([NH3+:14])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)([OH:4])=[O:3].Cl.[CH3:16]O>>[Cl-:1].[CH3:16][O:3][C:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2([NH3+:14])[CH2:13][CH2:12]2)=[CH:9][CH:10]=1)=[O:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 866348271-(4-Carboxyphenyl)cyclopropanaminium chloride

Product 1

HCID 86634826[1-(4-Methoxycarbonylphenyl)cyclopropyl]azanium chloride

Procedure

1-(4-Carboxyphenyl)cyclopropanaminium chloride from Example 16, Step 1 (4.17 mmol) in MeOH (10 mL) was heated to the reflux temperature, in the presence of HCl (4M in dioxane, 104 μL, 0.417 mmol), for 16 h and cooled to r.t. The mixture was concentrated to dryness and the residue was partitioned between EtOAc and a phosphate buffer (pH 10). The organic layer was washed with brine, dried (Na2SO4) and concentrated. The residue was dissolved in dioxane (10 mL) and excess HCl (4M in dioxane) was added. The mixture was then concentrated to dryness affording the desired product as a brown solid. The crude was used without further purification.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. customthe residue was partitioned between EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in dioxane (10 mL)
  7. additionexcess HCl (4M in dioxane) was added
  8. concentrationThe mixture was then concentrated to dryness

Sources & evidence

ORD record
ord-7926bc3300414b00b2e83cdc934febef
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Reaction notes

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