Pyrrolidine, 2-(2-chloroethyl)-1-methyl-, hydrochloride (1:1) → HCID 19423984, compound

HRID 743315Notes

Reaction equation

HRID 743315 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[OH:21])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].CC(C)([O-])C.[K+].Cl.Cl[CH2:30][CH2:31][CH:32]1[CH2:36][CH2:35][CH2:34][N:33]1[CH3:37]>CC(N(C)C)=O>[CH3:37][N:33]1[CH2:34][CH2:35][CH2:36][CH:32]1[CH2:31][CH2:30][O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][CH2:13][C:5]1[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 3017050Pyrrolidine, 2-(2-chloroethyl)-1-methyl-, hydrochloride (1:1)HCID 128887222-[2-(3,4,5-Trimethoxyphenyl)ethyl]phenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 19423984HCID 19423984, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Following a procedure similar to that described in Example 35(a), 1.00 g of 2-[2-(3,4,5-trimethoxyphenyl)ethyl]phenol (prepared as described in Preparation 28), 1.18 g of potassium t-butoxide and 0.958 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 0.900 g (yield 65%) 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-c48a83968d6447e9b9a6213dc80625ef
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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