HCID 54488810, compound → N,N'-(5-amino-1,3-phenylene)bisdecanamide

HRID 1757786Notes

Reaction equation

HRID 1757786 reaction equation
C1(COC(=O)[NH:10][C:11]2[CH:16]=[C:15]([NH:17][C:18](=[O:28])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:14]=[C:13]([NH:29][C:30](=[O:40])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH:12]=2)C=CC=CC=1>[Pd].C1COCC1>[NH2:10][C:11]1[CH:16]=[C:15]([NH:17][C:18](=[O:28])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:14]=[C:13]([NH:29][C:30](=[O:40])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH:12]=1

Participants

4

Reactant 1

HCID 54488810HCID 54488810, compound

Product 1

HCID 19389144N,N'-(5-amino-1,3-phenylene)bisdecanamideYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2.77 g (4.9 mmol) of [3,5-bis[(1-oxodecyl)amino]phenyl]carbamic acid phenylmethyl ester and 0.6g of 10% palladium on carbon in 60 ml of THF was shaken under a hydrogen atmosphere at room temperature and pressure for 8 hours. The catalyst was removed by filtration and the filtrate was concentrated at reduced pressure. The resultant solid was triturated with ether and filtered to give 1.94 g (92% yield, mp 152°-154°) of N,N'-(5-amino-1,3-phenylene) bisdecanamide.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated at reduced pressure
  3. customThe resultant solid was triturated with ether
  4. filtrationfiltered

Sources & evidence

ORD record
ord-0c96fe5839a447c1af2c06a65e4e4fdc
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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