Iodoethane → HCID 23503328, compound

HRID 1835271Notes

Reaction equation

HRID 1835271 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][C:35]=1[Cl:36])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C@H:13]([NH:17][C:18]([NH:20][C:21]2[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=2)=[O:19])[CH:14]([CH3:16])[CH3:15])[CH2:8][CH2:7]1.[I:37][CH2:38][CH3:39]>>[I-:37].[Cl:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][C:35]=1[Cl:36])[CH2:5][CH:6]1[CH2:7][CH2:8][N+:9]([CH2:38][CH3:39])([CH2:12][CH:13]([NH:17][C:18]([NH:20][C:21]2[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=2)=[O:19])[CH:14]([CH3:16])[CH3:15])[CH2:10][CH2:11]1

Participants

3

Reactant 2

HCID 6340IodoethaneHCID 10098735HCID 10098735, compound

Product 1

HCID 23503328HCID 23503328, compound

Procedure

A solution of 1-{1-(R)-[4-(3,4-dichlorobenzyl)piperidin-1-ylmethyl]-2-methylpropyl}-3-(3,4,5-trimethoxyphenyl)urea (0. 19 g, 0.353 mmoles) in iodoethane (4 ml) was stirred overnight at 68° C. degrees under argon. The yellow mixture was concentrated in vacuo and the crude product was flash chromatographed, eluting with 3%-4% methanol/methylene chloride to give 4-(3,4-dichlorobenzyl)-1-ethyl-1-{3-methyl-2-[3-(3,4,5-trimethoxyphenyl)ureido]butyl}piperidinium iodide (0.18 g) as a yellow solid.

Workup

  1. concentrationThe yellow mixture was concentrated in vacuo
  2. customchromatographed
  3. washeluting with 3%-4% methanol/methylene chloride

Sources & evidence

ORD record
ord-48a9cc9addf347109fb98d635c2bc6fb
Source dataset
uspto-grants-2004_08
Patent number
US06770650B2

Reaction notes

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