Water → 3,3-Dimethylbutyl 3-piperidinopropyl ether

HRID 604381Notes

Reaction equation

HRID 604381 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][O-:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Na+].[CH3:12][C:13]([CH3:18])([CH3:17])[CH2:14][CH2:15]Cl.C1OCCOCCOCCOCCOC1.O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O>[N:1]1([CH2:7][CH2:8][CH2:9][O:10][CH2:15][CH2:14][C:13]([CH3:18])([CH3:17])[CH3:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 3633615-Crown-5HCID 761111-Chloro-3,3-dimethylbutaneHCID 23694275HCID 23694275, compound

Product 1

HCID 97945573,3-Dimethylbutyl 3-piperidinopropyl ether

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium 3-piperidinopropanolate (5 mmol), 5 mmol of 3,3-dimethylbutyl chloride, a catalytic amount of tetrabutylammonium iodide, and 0.5 mmol of 15-crown-5 in 10 ml of dry dimethyl sulfoxide were refluxed for 12 hours. Water was added, and it was extracted with diethyl ether. The organic layer was purified by column chromatography on silica gel (eluent: methylene chloride/methanol (90/10), ammonia atmosphere). The solvent was removed under reduced pressure and the residue crystallized with oxalic acid from diethyl ether/ethanol.

Workup

  1. extractionit was extracted with diethyl ether
  2. customThe organic layer was purified by column chromatography on silica gel (eluent: methylene chloride/methanol (90/10), ammonia atmosphere)
  3. customThe solvent was removed under reduced pressure
  4. customthe residue crystallized with oxalic acid from diethyl ether/ethanol

Sources & evidence

ORD record
ord-49afa6cd8b4744a28766d5e2c34b0174
Source dataset
uspto-grants-2011_03
Patent number
US07910605B2

Reaction notes

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