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

Potassium Carbonate → 1-[1-(Tert-butoxycarbonyl)piperidin-4-ylmethyl]-4-(5-chlorobenzofuran-2-sulfonyl)-2-piperazinone

HRID 2186159
Notes
Print preview

Reaction equation

HRID 2186159 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]2[CH2:20][CH2:19][N:18]([S:21]([CH2:24]Cl)(=[O:23])=[O:22])[CH2:17][C:16]2=[O:26])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:27][C:28]1[CH:35]=[C:32]([CH:33]=O)[C:31]([OH:36])=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][N:15]2[CH2:20][CH2:19][N:18]([S:21]([C:24]3[O:36][C:31]4[CH:30]=[CH:29][C:28]([Cl:27])=[CH:35][C:32]=4[CH:33]=3)(=[O:23])=[O:22])[CH2:17][C:16]2=[O:26])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 234473251-[1-(Tert-butoxycarbonyl)piperidin-4-ylmethyl]-4-(chloromethanesulfonyl)-2-piperazinone

Product 1

HCID 234474431-[1-(Tert-butoxycarbonyl)piperidin-4-ylmethyl]-4-(5-chlorobenzofuran-2-sulfonyl)-2-piperazinoneYield 9.1%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-4-(chloromethanesulfonyl)-2-piperazinone (2.47 g), 5-chlorosalicylaldehyde (917 mg), potassium carbonate (810 mg) and DMF (30 ml) was stirred at 100° C. for 2 days, and the reaction solution was concentrated. To the residue was added water, and the mixture was extracted with ethyl acetate, washed with water and brine, dried and concentrated. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:4) to give colorless solid of 1-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]-4-(5-chlorobenzofuran-2-sulfonyl)-2-piperazinone (272 mg).

Workup

  1. concentrationthe reaction solution was concentrated
  2. additionTo the residue was added water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with water and brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-e2c42466e3864a5aac00a2d0abfac1b6
Source dataset
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06403595B1

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes