Hydrochloric Acid → 4-Benzyloxycarbonylamino-3,3-dimethylpiperidine

HRID 1865253Notes

Reaction equation

HRID 1865253 reaction equation
Cl.[CH2:2]([O:9][C:10]([NH:12][CH:13]1[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][C:14]1([CH3:27])[CH3:26])=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCOCC1>[CH2:2]([O:9][C:10]([NH:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][C:14]1([CH3:27])[CH3:26])=[O:11])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 690182114-Benzyloxycarbonylamino-1-t-butyloxycarbonyl-3,3-dimethylpiperidine

Product 1

HCID 222788384-Benzyloxycarbonylamino-3,3-dimethylpiperidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6 N HCl (200 ml) was added to a stirred solution of 4-benzyloxycarbonylamino-1-t-butyloxycarbonyl-3,3-dimethylpiperidine (350 g, 0.96 mol) in dioxane (200 ml). The resulting mixture was stirred for 1 hr and concentrated to dryness. The resultant residue was treated with water (3.0 L) water and was extracted with 1.0 L×2 ethyl acetate. The aqueous layer was basified with 2 M aqueous NaOH and extracted with 2.5 L×2 dichloromethane. Combined organic extract was washed with water, dried over Na2SO4 and concentrated to afford 4-benzyloxycarbonylamino-3,3-dimethylpiperidine in 89% (224 g) yield.

Workup

  1. concentrationconcentrated to dryness
  2. additionThe resultant residue was treated with water (3.0 L) water
  3. extractionwas extracted with 1.0 L×2 ethyl acetate
  4. extractionextracted with 2.5 L×2 dichloromethane
  5. extractionCombined organic extract
  6. washwas washed with water
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-94da4615137642e4b07857043403bab7
Source dataset
uspto-grants-2009_12
Patent number
US07626032B2

Reaction notes

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