HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Triethylamine → 4-(4-{[N-(2,6-dimethylphenyl)carbamoyl]methyl}piperazinyl)-3-hydroxy-N-(4-methoxyphenyl)butanamide

HRID 1271094
Notes
Print preview

Reaction equation

HRID 1271094 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:15])[CH2:11][CH:12]2[CH2:14][O:13]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:25]=1[NH:31][C:32](=[O:40])[CH2:33][N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1>C(O)C>[CH3:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[C:25]=1[NH:31][C:32]([CH2:33][N:34]1[CH2:35][CH2:36][N:37]([CH2:14][CH:12]([OH:13])[CH2:11][C:10]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[O:15])[CH2:38][CH2:39]1)=[O:40]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2608606Cvt-2738HCID 58844915N-(4-methoxyphenyl)-2-oxiran-2-ylacetamide

Product 1

HCID 184526914-(4-{[N-(2,6-dimethylphenyl)carbamoyl]methyl}piperazinyl)-3-hydroxy-N-(4-methoxyphenyl)butanamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of crude N-(4-methoxyphenyl)-2-oxiran-2-ylacetamide (10) in ethanol (2.5 mL) was added triethylamine (0.5 mL), followed by N-(2,6-dimethylphenyl)-2-piperazinylacetamide, a compound of formula (4) (150 mg), and the mixture was heated to reflux for 18 hours. Solvent was removed from the reaction mixture under reduced pressure, and the residue purified by column chromatography on silica gel, eluting with 5% MeOH/dichloromethane, to give 4-(4-{[N-(2,6-dimethylphenyl)carbamoyl]methyl}-piperazinyl)-3-hydroxy-N-(4-methoxyphenyl)butanamide, a compound of Formula I as an off-white solid.

Workup

  1. temperatureto reflux for 18 hours
  2. customSolvent was removed from the reaction mixture under reduced pressure
  3. customthe residue purified by column chromatography on silica gel
  4. washeluting with 5% MeOH/dichloromethane

Sources & evidence

ORD record
ord-c89104d315a44af39c213daad5a32b36
Source dataset
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07205303B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes