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

Ethanol → Bilastine

HRID 384013
Notes
Print preview

Reaction equation

HRID 384013 reaction equation
C([O:3][C:4](=[O:36])[C:5]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([C:22]3[N:26]([CH2:27][CH2:28][O:29][CH2:30][CH3:31])[C:25]4[CH:32]=[CH:33][CH:34]=[CH:35][C:24]=4[N:23]=3)[CH2:18][CH2:17]2)=[CH:10][CH:9]=1)([CH3:7])[CH3:6])C.[OH-].[Na+].C(O)C.O>C(O)CCC.C(OC(=O)C)C.C(O)(=O)C>[CH2:30]([O:29][CH2:28][CH2:27][N:26]1[C:25]2[CH:32]=[CH:33][CH:34]=[CH:35][C:24]=2[N:23]=[C:22]1[CH:19]1[CH2:20][CH2:21][N:16]([CH2:15][CH2:14][C:11]2[CH:10]=[CH:9][C:8]([C:5]([CH3:6])([CH3:7])[C:4]([OH:36])=[O:3])=[CH:13][CH:12]=2)[CH2:17][CH2:18]1)[CH3:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 66869688Ethyl 2-[4-(2-(4-(1-(2-ethoxyethyl)benzimidazole-2-yl)piperidine-1-yl)ethyl)phenyl]-2-methylpropanoate

Product 1

HCID 185460BilastineYield 85%

Reagents, catalysts & solvents 3

HCID 176
Acetic Acid
Solvent
HCID 2631-ButanolSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

In a reaction vessel, 2-[4-(2-{4-[1-(2-ethoxy-ethyl)-1H-benzoimidazol-2-yl]-piperidin-1-yl}-ethyl)-phenyl]-2-methyl-propionic acid ethylester (2.3 g) prepared in the Example 15, sodium hydroxide (0.6 g) and ethyl alcohol (13 mL) were introduced, and the mixture was reacted at 50-55° C. for 3 hours. Distilled water (20 mL) was added thereto, and acetic acid was added to control the pH to 7. Ethylacetate (50 mL) was added thereto, and the mixture was stirred to separate layers. The separated organic layer was condensed under reduced pressure. And, butanol (9 mL) was added and dissolved by heating. And then, it was cooled to precipitate crystals, and the crystals were filtered under reduced pressure to obtain 2-[4-(2-{4-[1-(2-ethoxy-ethyl)-1H-benzoimidazol-2-yl]-piperidin-1-yl}-ethyl)-phenyl]-2-methyl-propionic acid (1.84 g, yield 85%, HPLC purity 99% or more).

Workup

  1. additionwere introduced
  2. customthe mixture was reacted at 50-55° C. for 3 hours
  3. customto separate layers
  4. customcondensed under reduced pressure
  5. dissolutiondissolved
  6. temperatureby heating
  7. temperatureAnd then, it was cooled
  8. customto precipitate crystals
  9. filtrationthe crystals were filtered under reduced pressure

Sources & evidence

ORD record
ord-ea60f7c71b0749e49bf70391c713bf50
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08367704B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes