Pyrrolidine, 2-(2-chloroethyl)-1-methyl-, hydrochloride (1:1) → 1-Methyl-2-(2-{2-[2-(2-methylphenyl)ethyl]phenoxy}ethyl)pyrrolidine

HRID 743295Notes

Reaction equation

HRID 743295 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16].CC(C)([O-])C.[K+].Cl.Cl[CH2:25][CH2:26][CH:27]1[CH2:31][CH2:30][CH2:29][N:28]1[CH3:32]>CC(N(C)C)=O>[CH3:32][N:28]1[CH2:29][CH2:30][CH2:31][CH:27]1[CH2:26][CH2:25][O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 3017050Pyrrolidine, 2-(2-chloroethyl)-1-methyl-, hydrochloride (1:1)HCID 19424010Phenol, 2-[2-(2-methylphenyl)ethyl]-HCID 23665647Potassium tert-butoxide

Product 1

HCID 194239651-Methyl-2-(2-{2-[2-(2-methylphenyl)ethyl]phenoxy}ethyl)pyrrolidineYield 23%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Following a procedure similar to that described in Example 35(a), 1.00 g of 2-[2-(2-methylphenyl)ethyl]phenol (prepared as described in Preparation 24), 1.59 g of potassium t-butoxide and 1.73 g 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 350 mg (yield 23%) of the title compound as a solid.

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-8815f0d1efe64498a3fc3754840c6380
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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