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

HRID 641062

반응식

HRID 641062 반응식
[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]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2380342-(4-Aminophenyl)acetamideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 16775389HCID 16775389, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-9f939849868e4113b94cf81b2d00c8cc
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07692005B2

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