Di-p-tolylcarbodiimide → benzoic acid 1-(N,N'-di-p-tolyl-carbamimidoyloxy)-2,2,6,6-tetramethyl-piperidin-4-yl ester

HRID 1184985Notes

Reaction equation

HRID 1184985 reaction equation
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([O:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][C:3]1([CH3:20])[CH3:19].[C:21]1([CH3:37])[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[N:29][C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)=[CH:23][CH:22]=1>C1COCC1>[C:33]1([CH3:36])[CH:34]=[CH:35][C:30]([NH:29][C:28]([O:1][N:2]2[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([O:10][C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:4][C:3]2([CH3:20])[CH3:19])=[N:27][C:24]2[CH:23]=[CH:22][C:21]([CH3:37])=[CH:26][CH:25]=2)=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 69763Di-p-tolylcarbodiimideHCID 6881781-Hydroxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 58526176benzoic acid 1-(N,N'-di-p-tolyl-carbamimidoyloxy)-2,2,6,6-tetramethyl-piperidin-4-yl esterYield 63.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Hydroxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine (5.75 g, 20.7 mmol) [prepared as described in Example 6] and di-p-tolylcarbodiimide (4.8 g, 21.6 mmol) are dissolved in THF (40 ml) and the solution is stirred at room temperature for 17 hours. The solvent is evaporated and the residue is chromatographed on silica gel with hexane-ethyl acetate (9:1). The pure fractions are recrystallized from acetonitrile to afford 6.55 g of the title compound as a colorless solid, mp. 124-128° C.

Workup

  1. customThe solvent is evaporated
  2. customthe residue is chromatographed on silica gel with hexane-ethyl acetate (9:1)
  3. customThe pure fractions are recrystallized from acetonitrile

Sources & evidence

ORD record
ord-62e733b4542c43f492c9e657139f208b
Source dataset
uspto-grants-2014_03
Patent number
US08669398B2

Reaction notes

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