Ammonia → HCID 15279351, compound

HRID 234638Notes

Reaction equation

HRID 234638 reaction equation
[CH:1](=[C:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)[CH:2]([CH3:4])[CH3:3].[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C(C)C.[H-].[Na+].C1OC2(CCC(=O)CC2)OC1.[H][H].[NH3:51]>CS(C)=O.[Ni]>[CH:1](=[C:5]1[CH2:10][CH2:9][CH:8]([NH2:51])[CH2:7][CH2:6]1)[CH:2]([CH3:4])[CH3:3]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 18427326HCID 18427326, compoundHCID 86750219HCID 86750219, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15279351HCID 15279351, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

26.7 g (0.18 mol) of 4-isobutylidenecyclohexanone (prepared with isobutyltriphenylphosphonium bromide/sodium hydride and cyclohexane-1,4-dione monoethylene ketal in DMSO, followed by hydrolysis of the ketal) in 200 ml of ammonia-saturated methanol was subjected to reductive amination at 100° C. at a hydrogen pressure of 100 bar in the presence of 6 g of Raney nickel. After the catalyst had been removed by filtration and the methanol had been stripped off, the crude product was distilled on a thin-layer evaporator (135° C./0.6 bar). 16.5 g (61% of theory) of a pale yellow oil were obtained.

Workup

  1. customAfter the catalyst had been removed by filtration
  2. distillationthe crude product was distilled on a thin-layer evaporator (135° C./0.6 bar)
  3. custom16.5 g (61% of theory) of a pale yellow oil were obtained

Sources & evidence

ORD record
ord-2b6c2babaed749d8a82232224acd71fe
Source dataset
uspto-grants-1997_01
Patent number
US05595992

Reaction notes

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