Tetrahydrofuran → 1-(4-Formylbenzoyl)-4-isopropylpiperazine

HRID 13536

Reaction equation

[CH:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)([CH3:3])[CH3:2].C1COCC1.[OH-].[Na+].[CH:17]([C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)=[O:18]>O>[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:17]([C:19]2[CH:27]=[CH:26][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=2)=[O:18])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 2.5 °C

Procedure

4-Isopropyl-piperazine (79.53 g, 0.620 mol), THF (444 g, 5.04 mol), water (36 g, 2 mol) and a 50% solution of sodium hydroxide (130.6 g, 1.63 mol) were charged to a reaction vessel and cooled to 0-5° C. 4-Formyl-benzoyl chloride in THF (110.08 g, 0.630 mol) was added to the 4-isopropyl-piperazine reaction mixture while maintaining the temperature below about 10° C. The resulting white suspension was stirred at room temperature until the reaction was deemed complete. Water was added to the reaction slurry and the resulting hazy solution was filtered over Celite to remove insolubles. The filtered reaction solution was settled and the water layer was removed. The product/THF layer was dried sequentially with magnesium sulfate and molecular sieves. The product solution (KF≦0.5%) was stored at 5° C. for use without further manipulations.

Workup

temperaturewhile maintaining the temperature below about 10° C
filtrationthe resulting hazy solution was filtered over Celite
customto remove insolubles
customThe filtered reaction solution
customthe water layer was removed
dry with materialThe product/THF layer was dried sequentially with magnesium sulfate and molecular sieves
customwas stored at 5° C. for use without further manipulations

Sources & evidence

ORD record: ord-aec267aab7a3492ea2e6faaccc86e556
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728129B2

Linked notes

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