Dimethylformamide → HCID 24902687, compound

HRID 534819Notes

Reaction equation

HRID 534819 reaction equation
CC1C=CC(S([O:11][CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)(=O)=O)=CC=1.O[C:27]1[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:34][O:33][C:31]([C:30]1[CH:35]=[CH:36][C:27]([O:11][CH2:12][CH:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:17][CH2:18]2)=[CH:28][CH:29]=1)=[O:32]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 106428511-(tert-Butoxycarbonyl)-4-((p-toluenesulfonyloxy)methyl)piperidine

Product 1

HCID 24902687HCID 24902687, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of tert-butyl 4-({[(4-methylphenyl)sulfonyl]oxy}methyl)piperidine-1-carboxylate obtained in Reference Example 4 (8.0 g), methyl 4-hydroxybenzoate (3.1 g), potassium carbonate (5.53 g), and N,N-dimethylformamide (80 mL) was stirred at 60° C. for 16 h. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to provide the title compound (7.12 g, 100%) as crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bdb90123e0f64fcca959a8e4bd4a0fa3
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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