Potassium Carbonate → HCID 54214416, compound

HRID 1654161Notes

Reaction equation

HRID 1654161 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:14]=[CH:13][C:10]([O:11][CH3:12])=[C:7]([O:8][CH3:9])[CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:21]([O:28][CH2:29][C@@H:30]([CH3:33])[CH2:31]Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O>[CH2:21]([O:28][CH2:29][C@@H:30]([CH3:33])[CH2:31][N:2]([CH2:3][CH2:4][C:5]1[CH:14]=[CH:13][C:10]([O:11][CH3:12])=[C:7]([O:8][CH3:9])[CH:6]=1)[CH3:1])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77039N-MethylhomoveratrylamineHCID 7173934AC1Ogrol

Product 1

HCID 54214416HCID 54214416, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 10.93 g (0.056 mol) of N-methylhomoveratrylamine in 50 ml of abs. dimethylformamide was treated at 5° with 15.7 g of potassium carbonate and 13.6 g (0.056 mol) of (R)-(-)-3-benzyloxy-2-methylpropyl bromide [Helv. Chim. Acta 60, 940, (1977)]. The mixture was stirred at room temperature for 18 hours and then evaporated under reduced pressure. The residue was taken up in a mixture of water and ethyl acetate. The organic extracts were dried over magnesium sulphate and evaporated under reduced pressure. The residue was distilled at 218°/260 Pa. The N-[(S)-3-(benzyloxy)-2-methylpropyl]-3,4-dimethoxy-N-methylphenethylamine, which was obtained as a colourless oil, was used directly in the next step. [α]D ;20 =+7.3° (c=1, ethanol).

Workup

  1. customevaporated under reduced pressure
  2. additionThe residue was taken up in a mixture of water and ethyl acetate
  3. dry with materialThe organic extracts were dried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. distillationThe residue was distilled at 218°/260 Pa

Sources & evidence

ORD record
ord-57956e7c12ed483f9e682737b911e79c
Source dataset
uspto-grants-1995_04
Patent number
US05405866

Reaction notes

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