1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine → HCID 67291498, compound

HRID 736570Notes

Reaction equation

HRID 736570 reaction equation
[CH3:1][C:2]1([CH3:12])[N:7]([OH:8])[C:6]([CH3:10])([CH3:9])[CH2:5][CH:4]([OH:11])[CH2:3]1.CN(CCN(CCN(C)C)C)C.Cl[CH:26]([CH3:36])[C:27]([NH:29][CH2:30][CH2:31][CH2:32][N:33]([CH3:35])[CH3:34])=[O:28]>Cl[Cu]>[CH3:35][N:33]([CH3:34])[CH2:32][CH2:31][CH2:30][NH:29][C:27](=[O:28])[CH:26]([O:8][N:7]1[C:2]([CH3:12])([CH3:1])[CH2:3][CH:4]([OH:11])[CH2:5][C:6]1([CH3:10])[CH3:9])[CH3:36]

Participants

5

Reactant 3

HCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 18196PentamethyldiethylenetriamineHCID 16792302HCID 16792302, compound

Product 1

HCID 67291498HCID 67291498, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Procedure

4-Hydroxy-TEMPO (25.84 g, 0.15 mol), CuCl (29.7 g, 0.3 mol), PMDETA (52.0 g, 0.3 mol) and 2-chloro-N-(3-dimethylamino-propyl)-propionamide (35.75 g, 0.18 mol) are reacted as described in Example A3. The final purification of the residue after the extractive workup is performed by crystallization from toluene (45 ml) and hexane (50 ml) to afford 31.13 g of the title compound as a white solid, mp. 85-88° C.

Workup

  1. customThe final purification of the residue after the extractive workup
  2. customis performed by crystallization from toluene (45 ml) and hexane (50 ml)

Sources & evidence

ORD record
ord-09c40546898c4602b230fd42a43fbd89
Source dataset
uspto-grants-2009_09
Patent number
US07595359B2

Reaction notes

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