3-(Octadecyloxy)-5-(3-phenoxypropoxy)phenylcarbamic acid phenylmethyl ester → 3-(Octadecyloxy)-5-(3-phenoxypropoxy)benzenamine

HRID 1110249Notes

Reaction equation

HRID 1110249 reaction equation
C1(COC(=O)[NH:10][C:11]2[CH:16]=[C:15]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:14]=[C:13]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH:12]=2)C=CC=CC=1>[Pd].C1COCC1.C(OCC)(=O)C>[CH2:29]([O:28][C:13]1[CH:12]=[C:11]([NH2:10])[CH:16]=[C:15]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:14]=1)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]

Participants

5

Reactant 1

HCID 152328353-(Octadecyloxy)-5-(3-phenoxypropoxy)phenylcarbamic acid phenylmethyl ester

Product 1

HCID 152328363-(Octadecyloxy)-5-(3-phenoxypropoxy)benzenamineYield 92.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 10.9 g of 3-(octadecyloxy)-5-(3-phenoxypropoxy)phenylcarbamic acid phenylmethyl ester and 1.2 g of 10% palladium on carbon in 200 ml of THF and 50 ml of ethyl acetate was stirred under a hydrogen atmosphere at room temperature for 17 hours. The catalyst was removed by filtration and the filtrate was concentrated to a solid which was recrystallized from ethyl acetate-hexane to give 8.0 g (92% yield, mp 74°-76°) of 3-(octadecyloxy)-5-(3-phenoxypropoxy)benzenamine. The structure was confirmed by nmr and mass spectra.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated to a solid which
  3. customwas recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-4193c42a419144039a77de125a125034
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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