Tetrahydrofuran → 2-(4-Hydroxy-2,2,6,6-tetramethyl-piperidin-1-yl)-1,3-di-p-tolyl-isourea

HRID 1184990Notes

Reaction equation

HRID 1184990 reaction equation
[CH3:1][C:2]1([CH3:12])[N:7]([O])[C:6]([CH3:10])([CH3:9])[CH2:5][CH:4]([OH:11])[CH2:3]1.[H][H].[C:15]1([CH3:31])[CH:20]=[CH:19][C:18]([N:21]=[C:22]=[N:23][C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)=[CH:17][CH:16]=1.C1C[O:35]CC1>>[OH:11][CH:4]1[CH2:3][C:2]([CH3:12])([CH3:1])[N:7]([O:35][C:22](=[N:23][C:24]2[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=2)[NH:21][C:18]2[CH:19]=[CH:20][C:15]([CH3:31])=[CH:16][CH:17]=2)[C:6]([CH3:10])([CH3:9])[CH2:5]1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 69763Di-p-tolylcarbodiimideHCID 137994TempolHCID 178418361HCID 178418361, compound2×

Product 1

HCID 585261802-(4-Hydroxy-2,2,6,6-tetramethyl-piperidin-1-yl)-1,3-di-p-tolyl-isourea

Procedure

4-Hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl (1.9 g, 11 mmol) is dissolved in THF (40 ml) and hydrogenated in the presence of 0.035 g Pt (5% on carbon) catalyst using 4 bar hydrogen pressure. The hydrogen uptake stops after approximately one hour. The reaction mixture is then filtered and mixed with the solution of bis-p-tolyl-carbodiimide (2.45 g, 11 mmol) in THF (30 ml). The solution is stirred under argon at room temperature for 16 hours and concentrated. The residue is chromatographed on silica gel with hexane-ethyl acetate (1:1) and the pure fractions are crystallized from ethyl acetate to afford 1.6 g of the title compound as a colorless solid, mp. 124-126° C.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. concentrationconcentrated
  3. customThe residue is chromatographed on silica gel with hexane-ethyl acetate (1:1)
  4. customthe pure fractions are crystallized from ethyl acetate

Sources & evidence

ORD record
ord-4fe92e9146c04b1e88aafceca9fb7863
Source dataset
uspto-grants-2014_03
Patent number
US08669398B2

Reaction notes

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