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

HRID 2045828Notes

Reaction equation

HRID 2045828 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-hydrazineHCID 534729381-Chloro-3-(4-fluorophenyl)hex-5-en-3-ol

Product 1

HCID 58256489HCID 58256489, compoundYield 7.2%

Conditions

Temperature
140 °C

Procedure

1-chloro-3-(4-fluorophenyl)hex-5-en-3-ol (20 mg, 0.088 mmol) and 1-methyl-1-phenylhydrazine (640 mg, 5.26 mmol) were combined and heated in a microwave for 10 min at 120° C. and for 20 min at 140° C. The crude mixture was purified by chromatography on a silica gel cartridge eluted with an EtOAc/hexanes gradient followed by preparative HPLC to afford 3-(4-fluorophenyl)-1-(2-methyl-2-phenylhydrazinyl)hex-5-en-3-ol (2 mg). LC-MS Method 1 m/z=315 (M+1).

Workup

  1. customThe crude mixture was purified by chromatography on a silica gel cartridge
  2. washeluted with an EtOAc/hexanes gradient

Sources & evidence

ORD record
ord-9b12e8f8d0274b8c9e55779d1f796c5f
Source dataset
uspto-grants-2013_11
Patent number
US08592409B2

Reaction notes

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