Pyrrolidine, 2-(2-chloroethyl)-1-methyl-, hydrochloride (1:1) → 1-Methyl-2-(2-{2-[2-(3-methylphenyl)ethyl]phenoxy}ethyl)pyrrolidine

HRID 743287Notes

Reaction equation

HRID 743287 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])[CH:5]=[CH:6][CH:7]=1.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:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=1

Participants

5

Reactant 3

HCID 3017050Pyrrolidine, 2-(2-chloroethyl)-1-methyl-, hydrochloride (1:1)HCID 106323412-[2-(3-Methylphenyl)ethyl]phenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 107847231-Methyl-2-(2-{2-[2-(3-methylphenyl)ethyl]phenoxy}ethyl)pyrrolidineYield 11%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Following a procedure similar to that described in Example 35(a), 1.00 g of 2-[2-(3-methylphenyl)ethyl]phenol (prepared as described in Preparation 25), 1.05 g of potassium t-butoxide and 0.870 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 150 mg (yield 11%) of the title compound as an 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-30038e2b85b74399accb621776fc07b9
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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