Potassium Carbonate → N-pentyl-N-phenethyl-3-methoxy-phenethylamine

HRID 847405Notes

Reaction equation

HRID 847405 reaction equation
Br.[CH2:2]([NH:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:21](I)[CH2:22][CH2:23][CH2:24][CH3:25].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:21]([N:10]([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)[CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123351-IodopentaneHCID 19881396N-phenethyl-3-methoxyphenethylamine hydrobromide

Product 1

HCID 19881397N-pentyl-N-phenethyl-3-methoxy-phenethylamine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

13.4 g of N-phenethyl-3-methoxyphenethylamine hydrobromide [prepared as in French patent No. 2,356,417, Example 1], 200 ml of acetone, 22 ml of pentyl iodide and 29.3 g of potassium carbonate were refluxed for 4 hours and were vacuum filtered. The filter was washed with acetone and the filtrate was concentrated to dryness under reduced pressure. The 30 g of residue were chromatographed on silica (eluant: cyclohexane - ethyl acetate 7-3) to obtain 11.4 g of pure N-pentyl-N-phenethyl-3-methoxy-phenethylamine.

Workup

  1. filtrationfiltered
  2. washThe filter was washed with acetone
  3. concentrationthe filtrate was concentrated to dryness under reduced pressure
  4. customThe 30 g of residue were chromatographed on silica (eluant: cyclohexane - ethyl acetate 7-3)

Sources & evidence

ORD record
ord-bcac320f8afe4c1094827a694c1c74a7
Source dataset
uspto-grants-1992_08
Patent number
US05141962

Reaction notes

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