N-methyl-N-phenyl-hydrazine → HCID 58256489, compound

HRID 2045831Notes

Reaction equation

Cl[CH2:2][CH2:3][C:4]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)([OH:8])[CH2:5][CH:6]=[CH2:7].[CH3:16][N:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH2:18]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:15][C:12]1[CH:13]=[CH:14][C:9]([C:4]([OH:8])([CH2:5][CH:6]=[CH2:7])[CH2:3][CH2:2][NH:18][N:17]([CH3:16])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 63 °C

Procedure

1-chloro-3-(4-fluorophenyl)hex-5-en-3-ol (58 mg, 0.25 mmol), 1-methyl-1-phenylhydrazine (500 mg, 4.09 mmol), and tetrabutylammonium iodide (92 mg, 0.25 mmol) were combined and heated in a microwave for 50 min at 63° C. The crude mixture was filtered and purified twice by chromatography on a silica gel cartridge eluted with an EtOAc/hexanes gradient to remove 1-methyl-1-phenylhydrazine. The residue was dissolved in Et2O and washed with 1 M aq HCl. The aqueous layer was treated with 1 M aq NaOH until a pH of 4 was reached, then extracted with Et2O. The organic layer was evaporated and the residue was further purified by preparative HPLC to provide 3-(4-fluorophenyl)-1-(2-methyl-2-phenylhydrazinyl)hex-5-en-3-ol (6 mg). LC-MS Method 1 m/z=315 (M+1).

Workup

filtrationThe crude mixture was filtered
custompurified twice by chromatography on a silica gel cartridge
washeluted with an EtOAc/hexanes gradient
customto remove 1-methyl-1-phenylhydrazine
dissolutionThe residue was dissolved in Et2O
washwashed with 1 M aq HCl
additionThe aqueous layer was treated with 1 M aq NaOH until a pH of 4
extractionextracted with Et2O
customThe organic layer was evaporated
customthe residue was further purified by preparative HPLC

Sources & evidence

ORD record: ord-4ed7b5b07172425f9061693c55d32649
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592409B2

Reaction notes

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