Water → 4-(Methoxymethyl)piperidine

HRID 1282001Notes

Reaction equation

HRID 1282001 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)=O)(C)(C)C.I[CH3:17].[H-].[Na+].O>CN(C=O)C>[CH3:17][O:15][CH2:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 47152834-(Methoxymethyl)piperidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.1 g (0.46 mmol) of 1-t-butoxycarbonyl-4-hydroxymethylpiperidine and 0.1 mL (1.6 mmol) of iodomethane in 2.5 mL of DMF was added 0.022 g (0.92 mmol) of NaH (80% dispersion in mineral oil). After 2 h, 10 mL of H2O was added to the reaction mixture and it was extracted with ether. The combined organic fractions were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ethyl acetate=4:1) to give the title compound.

Workup

  1. extractionwas extracted with ether
  2. washThe combined organic fractions were washed with sat'd NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chromatography (silica, hexanes:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-dd9a48cb5ccc45a083443b7d4d19caec
Source dataset
uspto-grants-2002_09
Patent number
US06455548B2

Reaction notes

Loading…