Cyclooctylamine → HCID 4722991, compound

HRID 2398298Notes

Reaction equation

HRID 2398298 reaction equation
[CH:1]1[C:6]([CH:7]=O)=[CH:5][C:4]2[O:9][CH2:10][O:11][C:3]=2[CH:2]=1.[CH:12]1([NH2:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.[Ni]>[CH:12]1([NH:20][CH2:7][C:6]2[CH:1]=[CH:2][C:3]3[O:11][CH2:10][O:9][C:4]=3[CH:5]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 2903CyclooctylamineHCID 6101p-Toluenesulfonic acidHCID 8438Piperonal

Product 1

HCID 4722991HCID 4722991, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

16.5 g of piperonal, 12,7a g of cyclooctylamine and a catalytical amount of p-toluene-sulfonic acid were hydrogenated for 6 hours in 500 ml of methanol over Raney nickel at 100° C/100 atmospheres gauge pressure. After removal of the catalyst, evaporation of the solution and treatment of the residue with methanolic HCl, there were obtained 23 g of N-cyclooctyl-3,4-methylenedioxy-benzylamine. Melting point 164°-165° C (from ethanol/ether).

Workup

  1. customAfter removal of the catalyst, evaporation of the solution and treatment of the residue with methanolic HCl

Sources & evidence

ORD record
ord-f01a8a3298514ec4ae5402dacdae5b5f
Source dataset
uspto-grants-1977_05
Patent number
US04024274

Reaction notes

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