Potassium Carbonate → N-diethoxyethyl-6-(4-phenylbutoxy)hexylamine

HRID 1936213Notes

Reaction equation

HRID 1936213 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH2:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[CH2:25]([O:27][CH:28]([O:31][CH2:32][CH3:33])[CH2:29]Br)[CH3:26]>CN(C=O)C>[CH2:25]([O:27][CH:28]([O:31][CH2:32][CH3:33])[CH2:29][NH:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 109669026-(4-Phenylbutoxy)hexan-1-amine

Product 1

HCID 69996075N-diethoxyethyl-6-(4-phenylbutoxy)hexylamineYield 42.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.77 g (11.12 mmol) 6-(4-phenylbutoxy)hexylamine in 20 ml DMF is added 1.54 g (11.16 mmol) K2CO3 and 1.68 g (11.17 mmol) bromoacetaldehyde diethylacetal. After allowing the mixture to stand for 20 hr at 80° C., DMF is distilled off at reduced pressure, and the resulting crude product in 30 ml CH2Cl2 is washed with 30 ml H2O. The CH2Cl2 phase is dried on anhydrous Na2SO4, concentrated to dryness and the residue is purified by column chromatography on silica gel (gradient CH2Cl2/AcOEt 1:1 to AcOEt), thereby yielding 1.73 g (42.6 %) N-diethoxyethyl-6-(4-phenylbutoxy)hexylamine as an oil.

Workup

  1. distillationDMF is distilled off at reduced pressure
  2. washthe resulting crude product in 30 ml CH2Cl2 is washed with 30 ml H2O
  3. dry with materialThe CH2Cl2 phase is dried on anhydrous Na2SO4
  4. concentrationconcentrated to dryness
  5. customthe residue is purified by column chromatography on silica gel (gradient CH2Cl2/AcOEt 1:1 to AcOEt)

Sources & evidence

ORD record
ord-e6bcae5a79c94454a1e1961280c3ed32
Source dataset
uspto-grants-2002_05
Patent number
US06388134B1

Reaction notes

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