Triethylamine → N-[2-[N-ethyl-N-(2-hydroxyethyl)amino]ethyl]phthalimide

HRID 2273614Notes

Reaction equation

HRID 2273614 reaction equation
[CH2:1]([NH:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16])[CH3:2].Br[CH2:18][CH2:19][OH:20].C(N(CC)CC)C>C(O)C>[CH2:1]([N:3]([CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16])[CH2:18][CH2:19][OH:20])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 108982-BromoethanolHCID 21748445N-[2-(ethylamino)ethyl]phthalimide

Product 1

HCID 52951944N-[2-[N-ethyl-N-(2-hydroxyethyl)amino]ethyl]phthalimideYield 72.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of compound 2 (15.00 g, 68.7 mmol) in anhydrous ethanol (300 mL) were successively added, under argon, 2-bromoethanol (14.8 mL, 0.21 mol) and triethylamine (29.0 mL, 0.21 mol). The mixture was stirred under reflux for 60 h. After cooling to room temperature, the solvent was evaporated under vacuum and the residue was chromatographed (SiO2, AcOEt/EtOH, 99/1, v/v) to give compound 3 (13.00 g, 49.6 mmol) as a white solid. Yield 72%; Rf (SiO2, AcOEt/EtOH, 99/1, v/v) 0.49; mp 56-58° C.; IR (KBr) ν 1018, 1387, 1405, 1702, 2825, 2959, 3400-3600 cm−1; 1H NMR (200 MHz, CDCl3) δ 0.93 (t, 3H, J=7.1 Hz), 2.58 (q, 2H, J=7.1 Hz), 2.68 (t, 2H, J=5.3 Hz), 2.76 (t, 2H, J=6.2 Hz), 3.11 (se, 1H), 3.53 (t, 2H, J=5.3 Hz), 3.77 (t, 2H, J=6.2 Hz), 7.71 (m, 2H), 7.82 (m, 2H); MS m/z 262 (M+, 1), 231 (11), 174 (21), 130 (8), 102 (100), 76 (10), 58 (29).

Workup

  1. temperatureunder reflux for 60 h
  2. customthe solvent was evaporated under vacuum
  3. customthe residue was chromatographed (SiO2, AcOEt/EtOH, 99/1

Sources & evidence

ORD record
ord-e6d7e71b12824ec5a5e3e8181a1824e2
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

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