Hydrochloric Acid → N-(1-(2-benzyloxy-5-nitrophenyl)-1-methylethyl)amine

HRID 1861969Notes

Reaction equation

HRID 1861969 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[C:18]([CH3:23])(C)[C:19](O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl.C1(P([N:41]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.Cl>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[C:18]([NH2:41])([CH3:23])[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 199401P,P-Diphenylphosphinic azideHCID 186221532-(2-Benzyloxy-5-nitrophenyl)-2-methylpropionic acid

Product 1

HCID 18622160N-(1-(2-benzyloxy-5-nitrophenyl)-1-methylethyl)amineYield 75%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of the compound (1.6 g) obtained in Example 563, methylene chloride (20 ml) and triethylamine (0.92 ml), diphenylphosphorylazide (1.37 ml) was added. The reaction mixture was stirred at room temperature for 10 h and 2 N HCl and chloroform were added. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. To the resulting residue, water (16 ml) and 1,4-dioxane (32 ml) were added. The reaction mixture was heated under reflux for 2 h and 2 N HCl and chloroform were added. After adding 2 N aqueous sodium hydroxide solution and chloroform to the aqueous layer, the organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was recrystallized from a mixture of ethyl acetate and n-hexane to give 1.09 g of the titled compound (yield, 75%).

Workup

  1. additionwas added
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionTo the resulting residue, water (16 ml) and 1,4-dioxane (32 ml) were added
  6. temperatureThe reaction mixture was heated
  7. temperatureunder reflux for 2 h
  8. addition2 N HCl and chloroform were added
  9. additionAfter adding 2 N aqueous sodium hydroxide solution and chloroform to the aqueous layer
  10. washthe organic layer was washed with a saturated aqueous sodium chloride solution
  11. dry with materialdried with anhydrous sodium sulfate
  12. distillationthe solvent was distilled off under reduced pressure
  13. customThe resulting residue was recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-c63efa60d7ce45b0b1d9d07ebe9896f5
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

Loading…