Sodium hydride → 2-{Hydroxy-[2-(4-methylpiperazin-1-yl)phenyl]-methyl}-thiomorpholin-3-one

HRID 992973Notes

Reaction equation

HRID 992973 reaction equation
[H-].[Na+].[NH:3]1[CH2:8][CH2:7][S:6][CH2:5][C:4]1=[O:9].[CH3:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=2[CH:19]=[O:20])[CH2:13][CH2:12]1>C1COCC1>[OH:20][CH:19]([C:18]1[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=1[N:14]1[CH2:13][CH2:12][N:11]([CH3:10])[CH2:16][CH2:15]1)[CH:5]1[S:6][CH2:7][CH2:8][NH:3][C:4]1=[O:9]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 884021,4-Tetrahydrothiazine-3-oneHCID 27955662-(4-Methylpiperazin-1-yl)benzaldehyde

Product 1

HCID 120830042-{Hydroxy-[2-(4-methylpiperazin-1-yl)phenyl]-methyl}-thiomorpholin-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (930 mg, 23.3 mmol of 60% oil dispersion) was washed with hexanes under a nitrogen atmosphere and suspended in 100 mL of anhydrous THF. Thiomorpholin-3-one (1.0 g, 8.55 mmol) was added, followed immediately by 2-(4-methylpiperazin-1-yl)-benzaldehyde (1.58 g., 7.75 mmol). The reaction was then heated to reflux overnight, cooled to room temperature and concentrated in vacuo. The residue was dissolved in methylene chloride and washed with aqueous ammonium chloride (NH4Cl) and saturated brine and then dried with MgSO4. Purification using flash chromatography gave 2-{hydroxy-[2-(4-methylpiperazin-1-yl)phenyl]-methyl}-thiomorpholin-3-one as a white solid, m.p. 137-139° C. Mass spectrum 322 (M+1).

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in methylene chloride
  5. washwashed with aqueous ammonium chloride (NH4Cl) and saturated brine
  6. dry with materialdried with MgSO4
  7. customPurification

Sources & evidence

ORD record
ord-35c278f89caf4d5eba65da705db126ab
Source dataset
uspto-grants-2002_10
Patent number
US06472388B2

Reaction notes

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