2,5-Dimethoxytetrahydrofuran → HCID 19031209, compound

HRID 1648575Notes

Reaction equation

HRID 1648575 reaction equation
[NH2:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:18][CH2:17][C:15]3=[O:16])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.CO[CH:29]1[CH2:33][CH2:32][CH:31](OC)O1>C(O)(=O)C>[N:1]1([C:2]2[CH:3]=[CH:4][C:5]([C:6]([N:8]3[CH2:9][CH2:10][CH:11]([N:14]4[C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[CH2:18][CH2:17][C:15]4=[O:16])[CH2:12][CH2:13]3)=[O:7])=[CH:25][CH:26]=2)[CH:29]=[CH:33][CH:32]=[CH:31]1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 14969527HCID 14969527, compound

Product 1

HCID 19031209HCID 19031209, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-[1-(4-Aminobenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril (500 mg) and 2,5-dimethoxytetrahydrofuran (0.19 ml) are refluxed-with heating for 2 hours in acetic acid. The solvent is concentrated and the residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1) and recrystallized from n-hexane to give 1-{1-[4-(1-pyrrolyl)benzoyl]-4-piperidinyl}-3,4-dihydrocarbostyril (228 mg) as light gray powder, m.p.: 153°-156° C.

Workup

  1. concentrationThe solvent is concentrated
  2. customthe residue is purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1)
  3. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-cb91a8670d164823a02f9268fc06bccf
Source dataset
uspto-grants-1995_07
Patent number
US05436254

Reaction notes

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