Sodium Chloride → HCID 19082296, compound

HRID 2398498Notes

Reaction equation

HRID 2398498 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:18]=[CH:17][C:13]([CH2:14][CH2:15][NH2:16])=[CH:12][C:11]=1[N+:19]([O-:21])=[O:20].[OH-].[Na+].[Cl-].[Na+]>CS(C)=O>[CH2:1]([O:9][C:10]1[CH:18]=[CH:17][C:13]([CH2:14][CH2:15][NH2:16])=[CH:12][C:11]=1[N+:19]([O-:21])=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 189583303-Nitrotyramine

Product 1

HCID 19082296HCID 19082296, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
85 °C

Procedure

A solution of 17.1 g. (0.1 m.) of benzyl bromide in 100 ml. of dimethylsulfoxide is added slowly to a stirred mixture of 18.2 g. (0.1 m.) of 4-hydroxy-3-nitrophenethylamine in 1 l. of dimethylsulfoxide and 60 ml. of 2N sodium hydroxide at 85° C. After addition is complete the reaction mixture is stirred at 85° C. for an additional two hours, poured into ice-water, saturated with sodium chloride and extracted with ethyl acetate. The organic extract is dried and concentrated to give 4-benzyloxy-3-nitrophenethylamine. The latter (2.72 g., 0.01 m.) in 50 ml. of toluene is refluxed azeotropically with 1.27 g. (0.012 m.) of benzaldehyde until water formation is completed (about one hour). Solvent is removed by distillation to leave the crude imine. Sodium borohydride (0.38 g., 0.01 m.) is then added to a solution of the above imine in 30 ml. of methanol over a period of 30 minutes and after stirring for an additional hour the reaction mixture is evaporated. The residue is treated with 2N hydrochloric acid and ether. The solid obtained is filtered and washed to give N-benzyl-4-benzyloxy-3-nitrophenethylamine hydrochloride.

Workup

  1. customat 85° C
  2. additionAfter addition
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. customis dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-297eeb6f2d2844c7ab9eb5034ba5c6fd
Source dataset
uspto-grants-1977_05
Patent number
US04024281

Reaction notes

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