Pyrrolidine, 2-(2-chloroethyl)-1-methyl-, hydrochloride (1:1) → HCID 19423837, compound

HRID 743305Notes

Reaction equation

HRID 743305 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.CC(C)([O-])C.[K+].Cl.Cl[CH2:28][CH2:29][CH:30]1[CH2:34][CH2:33][CH2:32][N:31]1[CH3:35]>CC(N(C)C)=O>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH2:28][CH2:29][CH:30]2[CH2:34][CH2:33][CH2:32][N:31]2[CH3:35])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 3

HCID 3017050Pyrrolidine, 2-(2-chloroethyl)-1-methyl-, hydrochloride (1:1)HCID 19423974HCID 19423974, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19423837HCID 19423837, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Following a procedure similar to that described in Example 35(a), 1.00 g of 2-[2-(3,5-dimethoxyphenyl)ethyl]phenol (prepared as described in Preparation 27), 1.30 g of potassium t-butoxide and 1.06 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 1.15 g (yield 80%) 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-109ff74cb6e0468cb2a87244f77861de
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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