Hydrochloric Acid → HCID 69676423, compound

HRID 919617Notes

Reaction equation

HRID 919617 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([N:13]2[CH2:18][CH2:17][CH:16]([CH3:19])[CH:15]([NH:20]C(=O)OC(C)(C)C)[CH2:14]2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl>O1CCOCC1>[NH2:20][CH:15]1[CH:16]([CH3:19])[CH2:17][CH2:18][N:13]([C:11](=[O:12])[CH2:10][NH:9][C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH2:14]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69676422HCID 69676422, compound

Product 1

HCID 69676423HCID 69676423, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Tert-butyl 1-(2-(3,5-dichlorophenylamino)acetyl)-4-methylpiperidin-3-ylcarbamate (150 mg, 0.36 mmol) was treated with dioxane.HCl (5 mL) at rt for 2 h. The solvent was concentrated in vacuo, the resulting residue was dissolved in water (10 mL) and treated with solid NaHCO3. The aqueous solution was extracted with EtOAc (3×25 mL) and the combined organic layers were dried over Na2SO4, concentrated in vacuo to yield the titled intermediate (100 mg, 87%), which was used next without further purification. LC-MS: m/z [M+1]=316.

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. dissolutionthe resulting residue was dissolved in water (10 mL)
  3. additiontreated with solid NaHCO3
  4. extractionThe aqueous solution was extracted with EtOAc (3×25 mL)
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ecb6afb903c24e41b85b3d38b6367036
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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