Trifluoroacetic acid → 3-(Octadecyloxy)-5-(phenylmethoxy)benzenamine

HRID 1110284Notes

Reaction equation

HRID 1110284 reaction equation
CC(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[C:10]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH:9]=1)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:23]([O:22][C:10]1[CH:9]=[C:8]([NH2:7])[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:11]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 193890303-(Octadecyloxy)-5-(phenylmethoxy)phenylcarbamic acid dimethylethyl ester

Product 1

HCID 193889513-(Octadecyloxy)-5-(phenylmethoxy)benzenamineYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 28 g of 3-(octadecyloxy)-5-(phenylmethoxy)phenylcarbamic acid dimethylethyl ester and 76 ml of trifluoroacetic acid in 700 ml of methylene chloride was kept at room temperature for 2 hours. The solution was concentrated at reduced pressure and the residue was extracted with methylene chloride. The extract was washed with NaHCO3 solution, dried and concentrated to a solid which was dissolved in 1000 ml of ether. The solution was treated with 21 ml of 3N HCl in ethanol. The hydrochloride salt which precipitated was filtered and treated with excess NaHCO3 to liberate the free base which was extracted with methylene chloride. The dried extract was concentrated at reduced pressure to give 20.4 g (89% yield, mp 57°-59°) of 3-(octadecyloxy)-5-(phenylmethoxy)benzenamine.

Workup

  1. concentrationThe solution was concentrated at reduced pressure
  2. extractionthe residue was extracted with methylene chloride
  3. washThe extract was washed with NaHCO3 solution
  4. customdried
  5. concentrationconcentrated to a solid which
  6. dissolutionwas dissolved in 1000 ml of ether
  7. additionThe solution was treated with 21 ml of 3N HCl in ethanol
  8. customThe hydrochloride salt which precipitated
  9. filtrationwas filtered
  10. additiontreated with excess NaHCO3
  11. extractionwas extracted with methylene chloride
  12. extractionThe dried extract
  13. concentrationwas concentrated at reduced pressure

Sources & evidence

ORD record
ord-1201da6a907b44afb7aa864a82f20c31
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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