Methylparaben → Methyl 4-[2-(N-BOC-4-Piperidinyl)ethyloxy]benzoate

HRID 265863

Reaction equation

HRID 265863 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[C:12]([N:19]1[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26]I)[CH2:21][CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]>CN(C=O)C.CCOC(C)=O>[C:12]([N:19]1[CH2:20][CH2:21][CH:22]([CH2:25][CH2:26][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=2)[CH2:23][CH2:24]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]

Participants

5

Reactant 2

HCID 7456MethylparabenHCID 9974426Tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylate

Product 1

HCID 10832539Methyl 4-[2-(N-BOC-4-Piperidinyl)ethyloxy]benzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 4-hydroxybenzoate (Aldrich) (0.4 g, 2.6 mmoles) 9-1 in DMF (10 ml) was treated with 2-(N-Boc-4-piperidinyl)ethyl iodide 1-4 (0.6 g, 1.77 mmoles) and CS2CO3 (1.15 g, 3.5 mmoles) with stirring at room temperature for 48 hours. The reaction mixture was diluted with EtOAc, washed with H2O, saturated NaHCO3, 10% KHSO4, brine dried (MgSO4) and concentrated. The residue was purified by flash chromatography on silica gel eluting with 20% EtOAc/hexanes to give pure 9-2. Rf 0.3.

Workup

  1. washwashed with H2O, saturated NaHCO3, 10% KHSO4, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography on silica gel eluting with 20% EtOAc/hexanes
  5. customto give pure 9-2

Sources & evidence

ORD record
ord-b79d2a287dc44b13910f9db9d2875f8f
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Linked notes

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