Tetrahydrofuran → (4-aminobenzyl)cyclohexylcarbamic Acid Benzyl Ester

HRID 1173935Notes

Reaction equation

HRID 1173935 reaction equation
[CH2:1]([O:8][C:9](=[O:27])[N:10]([CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.O.NN>CO.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[CH2:1]([O:8][C:9](=[O:27])[N:10]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=1)[CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 66941326cyclohexyl(4-nitrobenzyl)carbamic Acid Benzyl Ester

Product 1

HCID 66941928(4-aminobenzyl)cyclohexylcarbamic Acid Benzyl EsterYield 101%

Reagents, catalysts & solvents 2

HCID 16211236Trichloroiron;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

The compound (1.24 g) obtained in Example 87-1 was dissolved in methanol (12 ml) and THF (6.2 ml) and added with activated carbon (124 mg) and iron trichloride hexahydrate (12.4 mg), followed by thermal reflux for 0.5 hour. After standing to cool, the solution was added with hydrazine monohydrate (0.89 ml) and then subjected to thermal reflux for 3 hours. After completion of the reaction, the resultant was filtrated through Celite and the solvent was then distilled off. The residue was dissolved in chloroform and washed with water. The solution was dried with anhydrous magnesium sulfate. The solvent was distilled off, thereby obtaining the subject compound (1.15 g) as a yellow viscous liquid.

Workup

  1. temperatureby thermal reflux for 0.5 hour
  2. temperatureto cool
  3. temperaturethermal reflux for 3 hours
  4. customAfter completion of the reaction
  5. filtrationthe resultant was filtrated through Celite
  6. distillationthe solvent was then distilled off
  7. dissolutionThe residue was dissolved in chloroform
  8. washwashed with water
  9. dry with materialThe solution was dried with anhydrous magnesium sulfate
  10. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-50a3f51f8be7497e84fe7db6258d752c
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

Loading…