Lithium hydroxide, monohydrate → HCID 21187567, compound

HRID 1383335Notes

Reaction equation

HRID 1383335 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH3:22])[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>[CH3:22][N:7]1[C:8]2[C:13](=[C:12]([N:15]3[CH2:16][CH2:17][N:18]([CH3:21])[CH2:19][CH2:20]3)[CH:11]=[CH:10][CH:9]=2)[CH:14]=[C:6]1[C:4]([OH:5])=[O:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 15550248HCID 15550248, compound

Product 1

HCID 21187567HCID 21187567, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(2-(ethoxycarbonyl)-1-methylindol-4-yl)-4-methylpiperazine (0.117 g, 0.39 mmol), lithium hydroxide hydrate (0.035 g, 0.83 mmol, 2 equivalents) in tetrahydrofuran (2 mL) and water (0.5 mL) was heated at reflux under nitrogen for 16 hours. The resulting reaction solution was evaporated under reduced pressure, and the residue was directly chromatographed using silica gel (approximately 10 g) and elution with methylene chloride/methanol/ammonium hydroxide [5:1:0.1] afforded the title compound (0.097 g, 0.34 mmol, 91%) as a yellow solid: 1H NMR (CD3OD) δ7.20-7.12 (m, 2H), 7.08 (s, 1H), 6.58 (dd, J=1.1 and 7.1 Hz, 1H), 4.90 (s, exchangeable H), 4.03 (s, 3H), 3.38 (br t, 4H), 3.34 (s, 3H), 3.28 (br t, 4H); LRMS (m/z, relative intensity) 274 (18), 273 (M+, 100), 258 (11), 229 (11), 203 (39), 202 (46), 71 (32), 70 (23); HRMS calculated for C15H19N3O2 273.1479, found 273.1479.

Workup

  1. temperatureat reflux under nitrogen for 16 hours
  2. customThe resulting reaction solution
  3. customwas evaporated under reduced pressure
  4. customthe residue was directly chromatographed
  5. washsilica gel (approximately 10 g) and elution with methylene chloride/methanol/ammonium hydroxide [5:1:0.1]

Sources & evidence

ORD record
ord-fc74a7ae9d6d48b0b53e7840b32ec086
Source dataset
uspto-grants-2001_07
Patent number
US06255306B1

Reaction notes

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