Benzylethanolamine → HCID 18008929, compound

HRID 987526Notes

Reaction equation

HRID 987526 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([NH:19][CH2:20][CH2:21][OH:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)CCC>[CH2:12]([N:19]([C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10])[CH2:20][CH2:21][OH:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 4348Benzylethanolamine2×HCID 770041,4-Dibromo-2-nitrobenzene

Product 1

HCID 18008929HCID 18008929, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2,5-dibromonitrobenzene (40 g) and N-benzylethanolamine (40.4 ml) in 1-butanol (160 ml) was heated at reflux for 18 hours then a further portion (20.2 ml) of N-benzylethanolamine was added and refluxing was continued for a further hour. The reaction mixture was evaporated under reduced pressure (2.7 kPa) at 40° C. and the residue was treated with water (500 ml) and the mixture was then extracted three times with diethyl ether (250 ml). The combined organic extracts were washed with hydrochloric acid (180 ml, 1N), then with an aqueous sodium hydrogen carbonate solution (20 ml, 5%), then twice with distilled water (50 ml), then dried over magnesium sulphate and then evaporated under reduced pressure (2.7 kPa) at 40° C. The resulting brown oil (47.1 g) was subjected to flash chromatography on silica (0,040-0,063 mm) eluting with dichloromethane to give the title compound (19.66 g) as a red oil. 1H NMR, 400 MHz, (CD3)2SO: δ3.1 (t, 2H); 3.5 (q, 2H); 4.5 (s, 2H); 4.6 (t, 1H); 7.3 (m, 6H); 7.6 (dd, J=8 Hz and J=1.5 Hz, 1H); 8 (d, J=1.5 Hz, 1H). MS (EI): M+ 352 and 350 (5%), 321 and 319 (20%), 91 (100%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. temperaturerefluxing
  4. waitwas continued for a further hour
  5. customThe reaction mixture was evaporated under reduced pressure (2.7 kPa) at 40° C.
  6. additionthe residue was treated with water (500 ml)
  7. extractionthe mixture was then extracted three times with diethyl ether (250 ml)
  8. washThe combined organic extracts were washed with hydrochloric acid (180 ml, 1N)
  9. dry with materialwith an aqueous sodium hydrogen carbonate solution (20 ml, 5%), then twice with distilled water (50 ml), then dried over magnesium sulphate
  10. customevaporated under reduced pressure (2.7 kPa) at 40° C
  11. washeluting with dichloromethane

Sources & evidence

ORD record
ord-d184a9c566d749afa4b1aa7e27be8660
Source dataset
uspto-grants-2003_10
Patent number
US06632814B1

Reaction notes

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