4-Methylmorpholine → 1-(3-Hydroxyphenyl)-4-(4-methyl-1-piperazinyl)-4-oxo-1-butanone

HRID 1986398Notes

Reaction equation

HRID 1986398 reaction equation
CC([Si](C)(C)[O:6][C:7]1[CH:8]=[C:9]([C:13](=[O:19])[CH2:14][CH2:15][C:16]([OH:18])=O)[CH:10]=[CH:11][CH:12]=1)(C)C.[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[OH:6][C:7]1[CH:8]=[C:9]([C:13](=[O:19])[CH2:14][CH2:15][C:16]([N:26]2[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]2)=[O:18])[CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 688720744-(3-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}phenyl)-4-oxobutanoic acid

Product 1

HCID 688734701-(3-Hydroxyphenyl)-4-(4-methyl-1-piperazinyl)-4-oxo-1-butanoneYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under nitrogen, to a solution of the product of Step 1 (490 mg, 2.52 mmol) in DMF (10 mL), was added 1-methylpiperazine (505 mg, 5.04 mmol), HOBT (1.02 g, 7.6 mmol), HBTU (950 mg, 2.5 mmol), followed with 4-methylmorpholine (770 μL, 7.6 mmol). This mixture was then stirred at rt overnight. The reaction mixture was concentrated and the residue was purified with reverse phase HPLC (5% MeCN/H2O→50% MeCN/H2O), to afford the title compound as white solid (572 mg, 82%). MS (ES+) m/e 277 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified with reverse phase HPLC (5% MeCN/H2O→50% MeCN/H2O)

Sources & evidence

ORD record
ord-d1e2c2e0345946de83f16d488a35ecd2
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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