Acetic Acid → HCID 66798914, compound

HRID 1193376Notes

Reaction equation

HRID 1193376 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4](=O)[CH2:3][C:2]1=[O:8].CC(O)=O.CN.Cl.[BH3-][C:17]#[N:18].[Na+]>CO>[CH3:17][NH:18][CH:4]1[CH2:5][CH2:6][NH:1][C:2](=[O:8])[CH2:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 108878632,4-Piperidinedione

Product 1

HCID 66798914HCID 66798914, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Piperidine-2,4-dione (2.0 g, 25.126 mmol, 1.0 eq.) was dissolved in MeOH (20 ml); AcOH (0.1 ml) and CH3NH2.HCl (2.37 g, 35.398 mmol, 2.0 eq.) were added and stirring was carried out for 2 hours at RT. NaCNBH3 (3.29 g, 53.097 mmol, 3.0 eq.) was added in portions at 0° C. and the mixture was stirred for 14 hours at RT. After monitoring by TLC, the reaction mixture was filtered, the filtrate was concentrated under reduced pressure and the residue was used in the next stage without being purified further. Yield: 81% (1.814 g, 14.173 mmol)

Workup

  1. stirringthe mixture was stirred for 14 hours at RT
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customwithout being purified further

Sources & evidence

ORD record
ord-85244684d8004dccb77fdc6c87ce9cca
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

Loading…