2-Chloroethanol → HCID 18680421, compound

HRID 1835273Notes

Reaction equation

HRID 1835273 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.Cl[CH2:38][CH2:39][OH:40]>>[Cl-:1].[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][CH2:39][OH:40])([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 342-ChloroethanolHCID 10098735HCID 10098735, compound

Product 1

HCID 18680421HCID 18680421, compound

Conditions

Temperature
90 °C

Procedure

1-{1-(R)-[4-(3,4-Dichlorobenzyl)piperidin-1-ylmethyl]-2-methylpropyl}-3-(3,4,5-trimethoxyphenyl)urea (0.21 g) was dissolved in 2-chloroethanol (5 mL) and the solution heated in an oil bath at 90° C. After stirring under nitrogen for 1 day, the reaction mixture was cooled and then poured directly onto a pad of silica gel. Elution with 6% methanol in methylene chloride and then 11% methanol in methylene chloride, followed by solvent removal from the appropriate fractions gave 4-(3,4-dichlorobenzyl)-1-(2-hydroxyethyl)-1-{3-methyl-2-[3-(3,4,5-trimethoxyphenyl)ureido]butyl}piperidinium chloride (41.6 mg).

Workup

  1. temperaturethe reaction mixture was cooled
  2. additionpoured directly onto a pad of silica gel
  3. washElution with 6% methanol in methylene chloride
  4. custom11% methanol in methylene chloride, followed by solvent removal from the appropriate fractions

Sources & evidence

ORD record
ord-ad0f971b7a9c49a98122784823627cff
Source dataset
uspto-grants-2004_08
Patent number
US06770650B2

Reaction notes

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