1-Methylpiperazine → (E)-Methyl 11-(4-methylpiperazin-1-yl)dibenzo[b,f][1,4]oxazepine-8-carboxylate

HRID 1907778Notes

Reaction equation

Cl[C:2]1=[N:3][C:4]2[CH:16]=[C:15]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=[CH:13][C:5]=2[O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]1=2.[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>C1(C)C=CC=CC=1>[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([C:2]2=[N:3][C:4]3[CH:16]=[C:15]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=[CH:13][C:5]=3[O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]2=3)[CH2:24][CH2:23]1

Participants

Conditions

Temperature: 110 °C

Procedure

Compound 549 (1.06 g, 3.68 mmol) and 1-methylpiperazine (0.818 mL, 7.37 mmol) were dissolved in toluene (40 mL) and stirred at 110° C. for 16 h. The toluene was removed on the rotary evaporator. The crude product was dissolved in ethyl acetate and washed with water. The organic layer was separated and dried with Na2SO4, filtered and concentrated via rotary evaporation. The residue was purified via Isco employing a 0 to 50% methanol:ethyl acetate solvent gradient to afford compound 550 (0.86 g, 66%) as a white solid.

Workup

customThe toluene was removed on the rotary evaporator
dissolutionThe crude product was dissolved in ethyl acetate
washwashed with water
customThe organic layer was separated
dry with materialdried with Na2SO4
filtrationfiltered
concentrationconcentrated via rotary evaporation
customThe residue was purified via Isco

Sources & evidence

ORD record: ord-8e24ad2d7b6f41a68296d7665452ade8
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598168B2

Reaction notes

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