Hydrazine hydrate (1:1) → HCID 178420376, compound

HRID 1921258Notes

Reaction equation

HRID 1921258 reaction equation
[CH:1]1([C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:10][C:9]=2F)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.O.[NH2:24][NH2:25]>>[CH2:15]([O:14][C:11]1[CH:10]=[C:9]2[C:8]([C:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[N:24][NH:25]2)=[CH:13][CH:12]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67219163HCID 67219163, compound

Product 1

HCID 178420376HCID 178420376, compoundYield 45%

Procedure

A mixture of cyclopentyl (4-benzyloxy-2-fluorophenyl)methanone (40 g, 0.13 mol) in hydrazine hydrate (50 ml) was refluxed overnight. After cooling to room temperature, the solid was filtered, dissolved in EtOAc, then washed with aqueous NH4Cl and brine. The solution was dried over Na2SO4, filtered and concentrated under vacuum. Purification by flash chromatography (toluene/EtOAc 9/1) gave the expected product (13 g, 45% as solid).

Workup

  1. temperaturewas refluxed overnight
  2. filtrationthe solid was filtered
  3. dissolutiondissolved in EtOAc
  4. washwashed with aqueous NH4Cl and brine
  5. dry with materialThe solution was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customPurification by flash chromatography (toluene/EtOAc 9/1)

Sources & evidence

ORD record
ord-285e71c128f941e184001af9bfa42fb1
Source dataset
uspto-grants-2012_05
Patent number
US08173679B2

Reaction notes

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