Hydrazine hydrate (1:1) → HCID 86698018, compound

HRID 518865Notes

Reaction equation

HRID 518865 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]3[CH2:16][CH2:17][CH2:18][C@@H:12]3[CH2:11]2)=[CH:6][C:5]=1[O:19][CH:20]([CH3:22])[CH3:21])([O-])=O.O.NN>C(O)C.[Pd]>[CH2:11]1[N:10]([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[C:5]([O:19][CH:20]([CH3:22])[CH3:21])[CH:6]=2)[CH2:15][CH2:14][N:13]2[CH2:16][CH2:17][CH2:18][C@H:12]12

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86698017HCID 86698017, compound

Product 1

HCID 86698018HCID 86698018, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1.38 g of (8aR)-2-[4-nitro-3-(propan-2-yloxy)phenyl]octahydropyrrolo[1,2-a]pyrazine, 2.72 g of hydrazine hydrate and 240 mg of 10% palladium-on-carbon (240 mg, 5 mol %) in 30 ml of ethanol is heated at 80° C. (bath) for 1 h 30. The mixture is filtered on Clarcel and the filtrate is concentrated under vacuum, so as to obtain 1.23 g of 4-[(8aR)-hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]-2-(propan-2-yloxy)aniline in the form of a purple oil.

Workup

  1. filtrationThe mixture is filtered on Clarcel
  2. concentrationthe filtrate is concentrated under vacuum

Sources & evidence

ORD record
ord-b66def0a9eb1401f809b2fe14b8e169d
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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