Sodium Hydroxide → AN-465/43411221

HRID 46774

Reaction equation

HRID 46774 reaction equation
Br.[CH2:2]([NH:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+]>O>[CH2:2]([NH:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=1)[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 30486862-(3,4-Dimethoxyphenyl)-N-(2-phenylethyl)ethan-1-amine--hydrogen bromide (1/1)

Product 1

HCID 215356AN-465/43411221Yield 97.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

25 g of the latter hydrobromide were dissolved in 250 ml of hot water and the solution was cooled to 0° C. and made alkaline with 40 ml of 2 N sodium hydroxide. The mixture was extracted 3 times with 100 ml of ethyl acetate and the organic extracts were washed with water until the wash water had a pH of 7 to 8. The extracts were dried over sodium sulfate, were filtered and evaporated to dryness under reduced pressure to obtain 19 g of N-phenethyl-3,4-dimethoxyphenethylamine.

Workup

  1. extractionThe mixture was extracted 3 times with 100 ml of ethyl acetate
  2. washthe organic extracts were washed with water until the wash water
  3. dry with materialThe extracts were dried over sodium sulfate
  4. filtrationwere filtered
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-667f98f9fa514bd293cae9b10b6fc01d
Source dataset
uspto-grants-1979_11
Patent number
US04175136

Linked notes

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