Potassium Carbonate → HCID 18789954, compound

HRID 1106880Notes

Reaction equation

HRID 1106880 reaction equation
[Br:1][C:2]1[CH:24]=[C:23]([N+:25]([O-])=O)[CH:22]=[CH:21][C:3]=1[O:4][CH2:5][CH2:6][N:7]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)[CH3:8].[Sn](Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>Cl>[Br:1][C:2]1[CH:24]=[C:23]([NH2:25])[CH:22]=[CH:21][C:3]=1[O:4][CH2:5][CH2:6][N:7]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)[CH3:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24479Stannous ChlorideHCID 18789856HCID 18789856, compound

Product 1

HCID 18789954HCID 18789954, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
50 °C

Procedure

A portion (1.25 g. 2.73 mmol) of the 1-(2-bromo-4-nitrophenoxy)-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane produced in (3) above was slowly added to cooled conc. hydrochloric acid (50 ml), followed by adding of tin(II) chloride (2.1 g), stirring at 50° C. for 1 h and subsequent cooling. The reaction mixture was added to ice water and neutralized with an aqueous solution of potassium carbonate, followed by extraction with chloroform and drying with magnesium sulfate; subsequent concentration gave the end compound 1-(2-bromo-4-aminophenoxy)-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane (1 g).

Workup

  1. additionabove was slowly added
  2. extractionfollowed by extraction with chloroform
  3. dry with materialdrying with magnesium sulfate
  4. concentrationsubsequent concentration

Sources & evidence

ORD record
ord-e76375925318457c902f016eb2ae5f72
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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