Triethylamine → N,N-Dimethyl-2-aminoethyl 3-(3,5-Di-tertiary-butyl-4-hydroxyanilino)benzoate

HRID 36729

반응식

HRID 36729 반응식
[C:1]([C:5]1[CH:6]=[C:7]([CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]=1[OH:21])[NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=[O:13])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30]Cl.C(N(CC)CC)C>CN(C)C=O.C(OCC)C>[C:22]([C:19]1[CH:18]=[C:7]([CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:20]=1[OH:21])[NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([O:14][CH2:30][CH2:29][N:28]([CH3:32])[CH3:27])=[O:13])([CH3:25])([CH3:24])[CH3:23]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 601943-(3,5-DI-T-Butyl-4-hydroxyanilino)benzoic acidHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

생성물 1

HCID 22401581N,N-Dimethyl-2-aminoethyl 3-(3,5-Di-tertiary-butyl-4-hydroxyanilino)benzoate수율 23.4%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

Under a nitrogen atmosphere, 6.0 g (0.0176 mole) of 3-(3,5-di-tertiary-butyl-4-hydroxyanilino)benzoic acid (from Example 13) and 2.53 g (0.0176 mole) of 2-dimethylaminoethyl chloride hydrochloride were dissolved in 17 ml of N,N-dimethylformamide. To this mixture was added 4.9 ml (0.035 mole) of triethylamine and the reaction was heated at 100° C. for 25 hours. The reaction temperature was then raised to 120° C. and heating was continued for an additional 28 hours. The reaction mixture was diluted with 10 ml of diethyl ether, then filtered to remove triethylamine hydrochloride. The filtrate was diluted with additional diethyl ether and then shaken with cold 10% hydrochloric acid. A middle layer contained most of the product hydrochloride. It was diluted with water and ether, and basified with solid sodium carbonate. The ether extract was washed with saturated aqueous sodium chloride and then concentrated to give 1.7 g of a tan solid, m.p. 119°-120° C. This material was recrystallized first from 20 ml of cyclohexane and then from a mixture of 10 ml of ethanol and 3 ml of water to give 1.48 g of light yellow prisms of N,N-dimethyl-2-aminoethyl 3-(3,5-di-t-butyl-4-hydroxyanilino)benzoate m.p. 123°-124° C. Analysis: Calculated for C25H36N2O3 : % C, 72.8; % H, 8.8; % N, 6.8. Found: % C, 73.0; % H, 8.8; % N, 6.7.

후처리

  1. temperatureThe reaction temperature was then raised to 120° C.
  2. temperatureheating
  3. filtrationfiltered
  4. customto remove triethylamine hydrochloride
  5. additionThe filtrate was diluted with additional diethyl ether
  6. additionIt was diluted with water and ether
  7. extractionThe ether extract
  8. washwas washed with saturated aqueous sodium chloride
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-797bb4470cf240cf9ee86aae8687a61f
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05416113

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