Hydrazine hydrate (1:1) → HCID 178514436, compound

HRID 1516158Notes

Reaction equation

HRID 1516158 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)=O.O.[NH2:20][NH2:21]>C1(C)C=CC=CC=1>[F:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C@H:8]2[CH2:9][CH2:10][C@H:5]([C:3]([NH:20][NH2:21])=[O:2])[CH2:6][CH2:7]2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178501276HCID 178501276, compound

Product 1

HCID 178514436HCID 178514436, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of trans-4-(4-fluoro-phenoxy)-cyclohexanecarboxylic acid methyl ester (0.23 g, 0.93 mmol) and hydrazine hydrate (0.046 g, 0.91 mmol) was heated at 120° C. for 3.5 h. After cooling to room temperature the reaction mixture was suspended in toluene (70 ml). After evaporation of the solvent, the residue was suspended in toluene (70 ml) again. The solvent was evaporated and the residue was dried in high vacuo (1-2 mbar) to give the crude title compound (0.22 g, 96%) as white solid, which was used in the next step without further purification. MS m/e: 253 (M+H+).

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. customAfter evaporation of the solvent
  3. customThe solvent was evaporated
  4. customthe residue was dried in high vacuo (1-2 mbar)

Sources & evidence

ORD record
ord-3da89557d764425da2b828c2aefd051a
Source dataset
uspto-grants-2012_07
Patent number
US08227458B2

Reaction notes

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