Sodium Carbonate → 4-Amino-1-Boc-piperidine

HRID 323693Notes

Reaction equation

HRID 323693 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:15]O.Cl.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 12682914-Amino-1-Boc-piperidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1-t-Butoxycarbonyl piperidine-4-one (commercially available from Lancaster Chem) (39.9 g, 0.20 mol), THF (150 mL), H2O (300 mL), and H2NOH HCl (55.2, 0.80 mol) were dissolved together and Na2CO3 (55.2 g, 0.53 mol) was added in small portions. The mixture was stirred at 23° for 14 h, most of the THF was evaporated in vacuo, adjusted to pH>10 with 50% aq NaOH, extracted with EtOAc(5×50 mL) and concentrated to a white foam. Triturated with hexane, filtered and the solid was dried in vacuo to afford 40.31 g of the title compound.

Workup

  1. customwas evaporated in vacuo
  2. extractionextracted with EtOAc(5×50 mL)
  3. concentrationconcentrated to a white foam
  4. customTriturated with hexane
  5. filtrationfiltered
  6. customthe solid was dried in vacuo

Sources & evidence

ORD record
ord-02341a6e723e4093bfb77c11a9da5a3b
Source dataset
uspto-grants-2001_04
Patent number
US06214844B1

Reaction notes

Loading…