Hydrazine hydrate (1:1) → HCID 178514443, compound

HRID 1516172Notes

Reaction equation

HRID 1516172 reaction equation
C([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][C:13]2[CH:18]=[N:17][CH:16]=[CH:15][N:14]=2)[CH2:8][CH2:7]1)=O)C.O.[NH2:20][NH2:21]>>[N:14]1[CH:15]=[CH:16][N:17]=[CH:18][C:13]=1[O:12][C@H:9]1[CH2:10][CH2:11][C@H:6]([C:4]([NH:20][NH2:21])=[O:3])[CH2:7][CH2:8]1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178472482HCID 178472482, compound

Product 1

HCID 178514443HCID 178514443, compoundYield 23%

Conditions

Temperature
120 °C

Procedure

A mixture of cis/trans-4-(pyrazin-2-yloxy)-cyclohexanecarboxylic acid ethyl ester (1.11 g, 4.41 mmol) and hydrazine hydrate (0442 g, 8.83 mmol) was heated at 120° C. for 72 h. After cooling to room temperature the reaction mixture was partitioned between ethyl acetate (50 ml) and water (30 ml). The organic layer was separated. The aqueous layer was extracted with two 50 ml portions of ethyl acetate. The combined organic layers were washed with brine (30 ml), dried over anhydrous sodium sulfate and concentrated in vacuo. The crude cis/trans-hydrazide was triturated in ethyl acetate (5 ml). The precipitate was collected by filtration and dried in vacuo to give the crude title compound (0.236 g, 23%) as white solid, which was used in the next step without further purification. MS m/e: 237 (M+H+)

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. customwas partitioned between ethyl acetate (50 ml) and water (30 ml)
  3. customThe organic layer was separated
  4. extractionThe aqueous layer was extracted with two 50 ml portions of ethyl acetate
  5. washThe combined organic layers were washed with brine (30 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customwas triturated in ethyl acetate (5 ml)
  9. filtrationThe precipitate was collected by filtration
  10. customdried in vacuo

Sources & evidence

ORD record
ord-5c9db8ade69143c191532d44b85b48b8
Source dataset
uspto-grants-2012_07
Patent number
US08227458B2

Reaction notes

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