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

HRID 2045830Notes

Reaction equation

HRID 2045830 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]>>[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

3

Reactant 2

HCID 36299N-methyl-N-phenyl-hydrazine2×HCID 534729381-Chloro-3-(4-fluorophenyl)hex-5-en-3-ol

Product 1

HCID 58256489HCID 58256489, compoundYield 8.7%

Conditions

Temperature
140 °C

Procedure

1-chloro-3-(4-fluorophenyl)hex-5-en-3-ol (50 mg, 0.22 mmol) and 1-methyl-1-phenylhydrazine (60 mg, 0.49 mmol) were combined and heated in a microwave for 20 min at 140° C. Starting material was still evident by LC-MS and additional 1-methyl-1-phenylhydrazine (640 mg, 5.26 mmol) was added. The mixture was further heated in a microwave for 20 min at 140° C. The crude mixture was purified by chromatography on a silica gel cartridge eluted with an EtOAc/hexanes gradient and 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

  1. additionwas added
  2. temperatureThe mixture was further heated in a microwave for 20 min at 140° C
  3. customThe crude mixture was purified by chromatography on a silica gel cartridge
  4. washeluted with an EtOAc/hexanes gradient
  5. customfurther purified by preparative HPLC

Sources & evidence

ORD record
ord-6610029187f94247a9d51a6572012cd6
Source dataset
uspto-grants-2013_11
Patent number
US08592409B2

Reaction notes

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