Methylglyoxal → HCID 21202930, compound

HRID 1979088Notes

Reaction equation

HRID 1979088 reaction equation
[CH:1](=O)[C:2]([CH3:4])=[O:3].[NH2:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8]1>CCOCC>[CH2:13]([N:10]1[CH2:11][CH2:12][CH:7]([N:6]=[CH:1][C:2](=[O:3])[CH3:4])[CH2:8][CH2:9]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 880MethylglyoxalHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 21202930HCID 21202930, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of pyruvaldehyde (40% w/w solution in water, 0.49 mL, 0.57 g, 3.19 mmol) in 10 mL of Et2O at room temperature was added dropwise 4-amino-1-benzylpiperidine (0.5 mL, 0.46 g, 2.45 mmol). After 20 min, the solution was diluted with 40 mL of Et2O and washed with 2×5 mL of water. The solution was concentrated in vacuo to yield the imine product which was used as such in the subsequent step: 1H NMR (CDCl3) δ 7.62 (1H, s), 7.29 (5H, m), 3.53 (2H, s), 3.28 (1H, m), 2.91 (2H, m), 2.38 (3H, s), 2.15 (2H, m), 1.84 (2H, m), 1.69 (2H, m).

Workup

  1. washwashed with 2×5 mL of water
  2. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-5630696b95dc4dd5979ad9d1a15a361c
Source dataset
uspto-grants-2001_05
Patent number
US06239279B1

Reaction notes

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