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

HRID 1440415

Reaction equation

HRID 1440415 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bc856e42230c49ca82442971b3185390
Source dataset
uspto-grants-1996_03
Patent number
US05498745

Linked notes

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