Tetrahydrofuran → HCID 21187590, compound

HRID 1383334Notes

Reaction equation

HRID 1383334 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([N:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1)[CH:11]=[CH:10][CH:9]=2)=[O:5])C.O.[OH-].[Li+].O1CCCC1>O>[CH3:21][N:18]1[CH2:19][CH2:20][N:15]([C:12]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:13]=2[CH:14]=[C:6]([C:4]([OH:5])=[O:3])[NH:7]3)[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 155502451-(2-(ethoxycarbonyl)-1H-indol-4-yl)-4-methylpiperazine

Product 1

HCID 21187590HCID 21187590, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-(2-(ethoxycarbonyl)-1H-indol-4-yl)-4-methylpiperazine (0.91 g, 3.17 mmol), lithium hydroxide hydrate (0.136 g, 3.17 mmol, 1.0 equivalent), tetrahydrofuran (20 mL), and water (4 mL) was heated at reflux under nitrogen for 16 hours. The resulting reaction mixture was evaporated under reduced pressure, and the residue was chromatographed using silica gel (approximately 30 g) and elution with methylene chloride/methanol/ammonium hydroxide [3:2:0.2] to afford the title compound (0.40 g, 1.54 mmol, 49%) as a white solid: mp, 272-273° C.; R, =0.05 in methylene chloride/methanol/ammonium hydroxide [5:1:0.1]; 13C NMR (D2O) δ169.4, 145.0, 137.5, 132.9, 124.7, 120.7, 108.2, 107.3, 103.7, 58.7, 53.7, 51.0; LRMS (m/z, relative intensity) 260 (18), 259 (M+, 100), 244 (9), 215 (7), 170 (24); HRMS calculated for C14H17N3O2 259.1322, found 259.1325.

Workup

  1. temperatureat reflux under nitrogen for 16 hours
  2. customThe resulting reaction mixture
  3. customwas evaporated under reduced pressure
  4. customthe residue was chromatographed
  5. washsilica gel (approximately 30 g) and elution with methylene chloride/methanol/ammonium hydroxide [3:2:0.2]

Sources & evidence

ORD record
ord-e5ceba4b334244c2ab903fb48b9be35a
Source dataset
uspto-grants-2001_07
Patent number
US06255306B1

Reaction notes

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