Potassium Carbonate → 3-methoxy-N-[2-(3-methoxyphenyl)-ethyl]-N-propyl-benzene-ethanamine

HRID 66128Notes

Reaction equation

HRID 66128 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH2:10][C:11]([NH:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)=O)[CH:7]=[CH:8][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:30](I)[CH2:31][CH3:32]>CC(C)=O>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][N:13]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)[CH2:30][CH2:31][CH3:32])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 227557503-methoxy-N-[2-(3-methoxyphenyl)-ethyl]-benzene-ethanamide hydrochloride

Product 1

HCID 124780053-methoxy-N-[2-(3-methoxyphenyl)-ethyl]-N-propyl-benzene-ethanamineYield 97.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 8.75 g of the product of Step A, 17.5 g of calcined neutral potassium carbonate, 17.5 g of propyl iodide and 180 ml of acetone was refluxed for 61/2 hours under nitrogen and the mixture was then filtered. The filtrate was evaporated to dryness and the residue was taken up in ether. The ether solution was washed with water, dried and evaporated to dryness to obtain 8.3 g of 3-methoxy-N-[2-(3-methoxyphenyl)-ethyl]-N-propyl-benzene-ethanamine which was used as is for the next step.

Workup

  1. temperaturewas refluxed for 61/2 hours under nitrogen
  2. filtrationthe mixture was then filtered
  3. customThe filtrate was evaporated to dryness
  4. washThe ether solution was washed with water
  5. customdried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-5ee94f4a4866432ba586e76f53bf5f20
Source dataset
uspto-grants-1978_12
Patent number
US04130658

Reaction notes

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