Ethanolamine → HCID 21483797, compound

HRID 1415172Notes

Reaction equation

HRID 1415172 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[CH:5]1[C:15]2[CH2:14][CH2:13][C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[C:10](=O)[C:9]=2[CH:8]=[CH:7][CH:6]=1>>[OH:2][CH2:1][CH2:3][N:4]=[C:10]1[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:15]=2[CH2:14][CH2:13][C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]1=2

Participants

3

Reactant 2

HCID 700Ethanolamine2×HCID 14589Dibenzosuberone

Product 1

HCID 21483797HCID 21483797, compound

Procedure

600 ml. of ethanolamine are added to 208 g. of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one. The mixture is heated under reflux conditions in an inert gas atmosphere for 16 hours. The refluxing ethanolamine is recycled into the reaction vessel through a Soxhlet attachment filled with 2 × 130 g. of 4A molecular sieve (bead form, 2 mm; Merck). The resulting mixture is then evaporated. The residue is dissolved in ether. The ether solution is washed with water and extracted with ice-cold 1N nitric acid. The acid extracts are washed with ether, adjusted to a pH value of 10-12 by addition of cold concentrated sodium hydroxide solution and subsequently extracted with methylene chloride. The methylene chloride extract is washed with water, dried over calcium chloride and evaporated under reduced pressure. The N-(2-hydroxy-ethyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-imine which is obtained melts at 93°-94° C. after recrystallization from acetone/petroleum ether: 3:5.

Workup

  1. temperatureThe mixture is heated under reflux conditions in an inert gas atmosphere for 16 hours
  2. additionfilled with 2 × 130 g
  3. customThe resulting mixture is then evaporated
  4. dissolutionThe residue is dissolved in ether
  5. washThe ether solution is washed with water
  6. extractionextracted with ice-cold 1N nitric acid
  7. washThe acid extracts are washed with ether
  8. additionadjusted to a pH value of 10-12 by addition of cold concentrated sodium hydroxide solution
  9. extractionsubsequently extracted with methylene chloride
  10. extractionThe methylene chloride extract
  11. washis washed with water
  12. dry with materialdried over calcium chloride
  13. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7b10b0ec54e04e999824cd836b09cb2e
Source dataset
uspto-grants-1977_01
Patent number
US04003915

Reaction notes

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