Acetic Acid → HCID 22403109, compound

HRID 259755Notes

Reaction equation

HRID 259755 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C=O.[C:9](O)(=O)C.[CH2:13]([S:15]([C:18]1[CH:19]=[CH:20][C:21]([O:29][CH3:30])=[C:22]([C:24]2[NH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=1)(=[O:17])=[O:16])[CH3:14]>C(O)C>[CH2:13]([S:15]([C:18]1[CH:19]=[CH:20][C:21]([O:29][CH3:30])=[C:22]([C:24]2[NH:25][C:26]([CH2:9][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:27][CH:28]=2)[CH:23]=1)(=[O:16])=[O:17])[CH3:14]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 8082PiperidineHCID 139003532-[5-(Ethanesulfonyl)-2-methoxyphenyl]-1H-pyrrole

Product 1

HCID 22403109HCID 22403109, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of piperidine (0.027 g, 0.32 mmol) in dry ethanol (2 ml) at room temperature was treated with aqueous formaldehyde (40%; 0.030g, 0.34 mmol) and glacial acetic acid (0.027 g, 0.45 mmol). The mixture was stirred at room temperature for 30 mins then was added dropwise to a solution of 2-(5-ethylsulphonyl-2-methoxyphenyl)-1H-pyrrole (0.086 g, 0.32 mmol) in dry ethanol (1 ml). The reaction mixture was stirred at room temperature for 18 hours then evaporated in vacuo. Chromatography on alumina (Brockmann grade 1) with ethyl acetate as eluant gave the title compound (E2)as a waxy solid after trituration with pentane (0.082 g, 70%).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 hours
  2. customthen evaporated in vacuo

Sources & evidence

ORD record
ord-58162e5a4c4f4aa6b2cfe3cdbe0c7fc8
Source dataset
uspto-grants-1996_06
Patent number
US05523299

Reaction notes

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