1,2-Dichloroethane → HCID 86756163, compound

HRID 1277157Notes

Reaction equation

HRID 1277157 reaction equation
[C:1]([O:5]C(N1CCC(=O)CC1)=O)([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:16][NH2:17].C([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])C.[OH-:25].[Na+].Cl[CH2:28][CH2:29]Cl>>[C:1]([O:5][N:20]1[CH2:21][CH2:22][CH:29]([NH:17][CH3:16])[CH2:28][C:23]1=[C:24]=[O:25])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 6364545Methylamine hydrochloride

Product 1

HCID 86756163HCID 86756163, compound

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) and methylamine 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-0c62681f6a7240fca25e97de5aa98059
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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