Ethanol → HCID 117666925, compound

HRID 1526199Notes

Reaction equation

HRID 1526199 reaction equation
[CH3:1][N:2]1[C:7]2([CH2:12][CH2:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=3)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3]1.C(O)C>[Pd].O1CCCC1>[CH3:1][N:2]1[C:7]2([CH2:8][CH2:9][N:10]([C:13]3[CH:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=3)[CH2:11][CH2:12]2)[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 702EthanolHCID 117667273HCID 117667273, compound

Product 1

HCID 117666925HCID 117666925, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-methyl-9-(4-nitrophenyl)-1,9-diazaspiro[5.5]undecane (680 mg), ethanol (10 mL), and tetrahydrofuran (10 mL) was added 10% palladium-supported carbon (50% wet product) (150 mg), followed by stirring for 5 hours under a hydrogen gas atmosphere (1 atm). The reaction mixture was filtered through celite and then the solvent was evaporated under reduced pressure to obtain 4-(1-methyl-1,9-diazaspiro[5.5]undec-9-yl)aniline (0.6 g) as a pale purple solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a859044b7deb4af6abef79912d8bf1ba
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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