HCID 23316741, compound → HCID 23316727, compound

HRID 1982481Notes

Reaction equation

HRID 1982481 reaction equation
[CH2:1]([N:5]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:6]([CH3:19])[CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH3:4].[H][H]>C(O)C.[Pd]>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][CH2:7][CH:6]([CH3:19])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 23316741HCID 23316741, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23316727HCID 23316727, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 16.2 g (0.045 mol) of N-butyl-N-heptyl-α-methyl-4-nitrobenzenebutanamine in 182 ml of ethanol was hydrogenated at room temperature overnight in the presence of 1.6 g of 5% palladium-on-carbon. hydrogen uptake observed was 74% of theoretical. The reaction mixture was filtered through Celite and the filtrate was evaporated under reduced pressure. The resulting material indicated the presence of one spot by thin-layer chromatography and afforded 13.56 g of 4-amino-N-butyl-N-heptyl-α-methylbenzenebutanamine as an oil.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7b28061b7c934d9ab827c9e3b7c01bb8
Source dataset
uspto-grants-1986_06
Patent number
US04596827

Reaction notes

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