Benzyl Bromide → HCID 18762668, compound

HRID 430955Notes

Reaction equation

HRID 430955 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][C:5](=[O:8])[NH:4][C:3]1=[O:9].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(N(CC)CC)C>[CH2:10]([NH:1][CH:2]1[CH2:7][CH2:6][C:5](=[O:8])[NH:4][C:3]1=[O:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 1345083-Amino-2,6-piperidinedione

Product 1

HCID 18762668HCID 18762668, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of 0.50 g 3-aminopiperidine-2,6-dione (K. Fickentscher, Arch. Pharm. 1974, 307, 840-844), 1.5 ml triethylamine and 0.4 ml benzyl bromide was stirred for 20 h at 20° C. It was then evaporated, the residue taken up in 50 ml aqueous potassium carbonate solution (10% K2CO3) and the solution extracted twice with 40 ml ethyl acetate each. The organic phases were washed with 50 ml each of distilled water and saturated sodium chloride solution, dried over sodium sulfate and evaporated in vacuo. The residue was purified by flash chromatography on silica gel with a mixture of ethyl acetate/cyclohexane (2/1) containing 1% triethylamine as eluent, whereby 0.21 g (26% of theoretical) of the title compound was obtained as viscous oil.

Workup

  1. customIt was then evaporated
  2. extractionthe solution extracted twice with 40 ml ethyl acetate each
  3. washThe organic phases were washed with 50 ml each of distilled water and saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel with a mixture of ethyl acetate/cyclohexane (2/1)
  7. additioncontaining 1% triethylamine as eluent

Sources & evidence

ORD record
ord-1d089016284c484287a06a9baddc7555
Source dataset
uspto-grants-2003_12
Patent number
US06656937B2

Reaction notes

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