1,4-Dihydroxy-2,2,6,6-tetramethylpiperidine → HCID 21026383, compound

HRID 900409Notes

Reaction equation

HRID 900409 reaction equation
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].[OH:6][N:7]1[C:12]([CH3:14])([CH3:13])[CH2:11][CH:10]([OH:15])[CH2:9][C:8]1([CH3:17])[CH3:16]>ClCCCl>[CH2:1]([NH:3][C:4](=[O:5])[O:15][CH:10]1[CH2:11][C:12]([CH3:13])([CH3:14])[N:7]([O:6][C:4](=[O:5])[NH:3][CH2:1][CH3:2])[C:8]([CH3:17])([CH3:16])[CH2:9]1)[CH3:2]

Participants

4

Reactant 2

HCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineHCID 8022Ethyl isocyanate

Product 1

HCID 21026383HCID 21026383, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

20 ml (0.26 mol) of ethyl isocyanate are added dropwise under nitrogen to 10.0 g (0.058 mol) of 1,4-dihydroxy-2,2,6,6-tetramethylpiperidine, prepared as described by Paleos C. M. et al., loc. cit., in 100 ml of 1,2-dichloroethane. The mixture is stirred at 70° C. for 30 hours and then evaporated to dryness on a rotary evaporator. Recrystallization of the residue from xylene gives 14.4 g (77%) of the compound 117 as colourless crystals; melting point: 149-151° C.

Workup

  1. customprepared
  2. customevaporated to dryness on a rotary evaporator
  3. customRecrystallization of the residue from xylene

Sources & evidence

ORD record
ord-3942ab4d1a68489c9affbe9c55bf50e7
Source dataset
uspto-grants-2008_04
Patent number
US07358365B2

Reaction notes

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