Hydrochloric Acid → 4-[2-(Diethylamino)ethyl]aniline

HRID 2352994Notes

Reaction equation

HRID 2352994 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=O)=[CH:4][CH:3]=1.NC1C=CC(CC(N)=O)=CC=1.CSC.B.Cl.[OH-].[Na+]>C1COCC1>[CH2:14]([N:11]([CH2:12][CH3:13])[CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[CH:7][CH:6]=1)[CH3:15]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2380342-(4-Aminophenyl)acetamideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 167753892-(4-aminophenyl)-N,N-diethylacetamide

Product 1

HCID 225692664-[2-(Diethylamino)ethyl]anilineYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(4-aminophenyl)-N,N-diethylacetamide, (2-NB-2-A13; 1.5 g, 7.28 mmol) from Step 2 in anhydrous THF (15 mL) kept at 0° C. was added a 2 M solution of borane dimethylsulfide in THF (14.5 mL, 29 mmol) slowly. The reaction was allowed to warm to room temperature and stirred for 18 h. Hydrochloric acid (6N, 10 mL) was carefully added and the reaction was refluxed for 1 hour followed by cooling to room temperature and neutralization with 3N sodium hydroxide solution. Aqueous layer was separated and extracted with ethyl acetate (4×30 mL). Combined organic layer was dried over sodium sulfate, filtered and evaporated to provide 4-(2-(diethylamino)ethyl)aniline as a light-brown oil (1.25 g, 86%).

Workup

  1. customkept at 0° C.
  2. temperaturethe reaction was refluxed for 1 hour
  3. temperatureby cooling to room temperature
  4. customAqueous layer was separated
  5. extractionextracted with ethyl acetate (4×30 mL)
  6. dry with materialCombined organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-140a8eb4a30747d4a89f5e3ff5eb3008
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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