Hydrochloric Acid → 2-(3,5-dichlorophenylamino)-1-((S)-3-aminopiperidin-1-yl)ethanone

HRID 919595Notes

Reaction equation

HRID 919595 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([NH:19]C(=O)OC(C)(C)C)[CH2:14]2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([NH2:19])[CH2:14]2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69676426tert-butyl(S)-1-(2-(3,5-dichlorophenylamino)acetyl)piperidin-3-ylcarbamate

Product 1

HCID 696764492-(3,5-dichlorophenylamino)-1-((S)-3-aminopiperidin-1-yl)ethanoneYield 81.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl(S)-1-(2-(3,5-dichlorophenylamino)acetyl)piperidin-3-ylcarbamate (0.9 mg, 2.2 mmol) in 1,4-dioxane (5 mL) was added 4 N HCl in dioxane (10 mL) and the reaction mixture was stirred for 1 h. The reaction mixture was concentrated in vacuo and the resultant residue was dissolved in water and aqueous phase was adjusted to a pH 9 with sat. NaHCO3 and extracted with EtOAc (3×50 mL). The combined organic layer was dried over Na2SO4 and evaporated in vacuo to afford the titled intermediate (540 mg, 79%), which was used in the next step without purification. LCMS: m/z: [M+1]=302.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe resultant residue was dissolved in water
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-3a090cc853d549fbaa5e0e7c17763988
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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