Hydrochloric Acid → HCID 86756163, compound

HRID 565981Notes

Reaction equation

HRID 565981 reaction equation
[C:1]([O:5]C(N1CCC(=O)CC1)=O)([CH3:4])([CH3:3])[CH3:2].Cl.C([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])C.[OH-:23].[Na+]>ClCCCl>[C:1]([O:5][N:18]1[CH2:19][CH2:20][CH:19]([NH:18][CH3:21])[CH2:20][C:21]1=[C:22]=[O:23])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 86756163HCID 86756163, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of N-t-butoxycarbonylpiperidin-4-one (3 g; M. S. Ashwood et al., J. Chem. Soc. Perkin Trans. 1, 1995, 641-644) andmethylamine hydrochloride (1 g) were added triethylamine (2.1 ml) and 1,2-dichloroethane (50 ml). Under ice-cooling, to the mixture was added sodium triacetoxy boron hydride (4.5 g), and the mixture was stirred under nitrogen atmosphere at room temperature for 4 hours. The mixture was neutralized with sodium hydroxide, concentrated and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated to give 1-t-butoxy-carbonyl-4-methylaminopiperidine (3.1 g) as colorless oil.

Workup

  1. temperatureUnder ice-cooling, to the mixture
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customUnder reduced pressure, the solvent was evaporated

Sources & evidence

ORD record
ord-93d95fd72e0343a98d2aea459c9b948b
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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