2-(2-Phenylethyl)phenol → 1-Methyl-2-{2-[2-(2-phenylethyl)phenoxy]ethyl}pyrrolidine

HRID 743285Notes

Reaction equation

HRID 743285 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].Cl.Cl[CH2:24][CH2:25][CH:26]1[CH2:30][CH2:29][CH2:28][N:27]1[CH3:31]>CC(N(C)C)=O>[CH3:31][N:27]1[CH2:28][CH2:29][CH2:30][CH:26]1[CH2:25][CH2:24][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 27490412-(2-Phenylethyl)phenolHCID 3017050Pyrrolidine, 2-(2-chloroethyl)-1-methyl-, hydrochloride (1:1)HCID 23665647Potassium tert-butoxide

Product 1

HCID 107837421-Methyl-2-{2-[2-(2-phenylethyl)phenoxy]ethyl}pyrrolidineYield 34.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Following a procedure similar to that described in Example 35(a), 900 mg of 2-(2-phenylethyl)phenol (prepared as described in Preparation 19), 1.02 g of potassium t-butoxide and 836 mg of 2-(2-chloroethyl)-1-methylpyrrolidine hydrochloride were reacted in 10 ml of dimethylacetamide. The mixture was then worked up as described in Example 35(a), and the crude product thus obtained was purified by column chromatography through silica gel, using a 10:1 by volume mixture of methylene chloride and methanol as the eluent, to give 480 mg of the title compound as a colorless oil.

Workup

  1. customthe crude product thus obtained
  2. customwas purified by column chromatography through silica gel
  3. additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-8a020ab3c56740c5abe10286f2f54da9
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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