Sodium Hydroxide → HCID 21897120, compound

HRID 916095Notes

Reaction equation

HRID 916095 reaction equation
[CH2:1]([N:5]([CH2:23][CH2:24][CH3:25])[C:6]1[N:11]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([Cl:21])[CH:14]=2)[N:9]=[C:8](Cl)[N:7]=1)[CH2:2][CH2:3][CH3:4].[CH3:26][N:27]1[CH2:32][CH2:31][CH:30]([NH:33][CH3:34])[CH2:29][CH2:28]1.[OH-].[Na+]>O1CCOCC1>[OH-:19].[NH4+:5].[CH2:1]([N:5]([CH2:23][CH2:24][CH3:25])[C:6]1[N:11]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([Cl:21])[CH:14]=2)[N:9]=[C:8]([N:33]([CH3:34])[CH:30]2[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][CH2:29]2)[N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 5663231-Methyl-4-(methylamino)piperidineHCID 21897143HCID 21897143, compound

Product 2

HCID 14923Ammonium HydroxideHCID 21897120HCID 21897120, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a sample of 110 (1.323 g, 3.4 mmol) dissolved in 1,4-dioxane (25 mL) was added a solution of N-methyl-4(methylamino)piperidine (0.4 mL, 3.4 mmol) in 1,4-dioxane (1 mL) followed by the addition of NaOH (1.4 mL, 2.5 N, 3.4 mmol). The reaction mixture was allowed to stir at reflux for about 2 hours under nitrogen. The reaction mixture was extracted 3 times with dichloromethane; the combined organic layers were washed with brine and dried over potassium carbonate. The sample was concentrated on the rotary evaporator and the resulting solid was dried overnight under vacuum. Column chromatography (silica gel, 90:9:1 dichloromethane:methanol:conc. ammonium hydroxide) yielded light brown solid compound 111 (527 mg, 33%), mp 68° C.; TLC (silica gel, 90:9:1 CH2Cl2:CH3OH:conc. NH4OH), Rf 0.46; HPLC: ODS-3V C18, 40:30:30 [KH2PO4 (0.01 M, pH 3.2): CH3OH:CH3CN], 264 mn, Rt 41.6 min, 90.8% purity); MS (ESI): m/z 476 (M+H, 28.5), 261 (20.2), 260 (52.8), 259 (100), 239 (18.6), 239 (50.6).

Workup

  1. temperatureat reflux for about 2 hours under nitrogen
  2. extractionThe reaction mixture was extracted 3 times with dichloromethane
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over potassium carbonate
  5. concentrationThe sample was concentrated on the rotary evaporator
  6. customthe resulting solid was dried overnight under vacuum

Sources & evidence

ORD record
ord-4ce941ab4cd747ce9fa33d75c5bfb5f0
Source dataset
uspto-grants-2007_09
Patent number
US07268134B2

Reaction notes

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