Triethylamine → HCID 21409982, compound

HRID 1973524Notes

Reaction equation

HRID 1973524 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:16]([CH2:18][CH2:19]Cl)[CH3:17])=[C:6]([CH:15]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].[NH2:21][CH2:22][CH2:23][CH2:24]O.C(N(CC)CC)C>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:16]([CH3:17])[CH2:18][CH2:19][N:21]3[CH2:22][CH2:23][CH2:24][O:8][C:7]3([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]=2[CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90863-Amino-1-propanolHCID 21823034HCID 21823034, compound

Product 1

HCID 21409982HCID 21409982, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5.0 g. (16 mmole) of 5-chloro-2-(2-chloroethylmethylamino)benzophenone, 3.75 g. (50 mmole) of 3-aminopropanol, 50 ml. of triethylamine and 250 ml. of ethanol was stirred at reflux for 48 hours. The reaction mixture was then evaporated to a residue which was washed with water, dissolved in methylene chloride and chromatographed over a column of Florisil. The first fraction yielded the recovery of 2.7 g. of starting material. Elution with acetone, ethanol, methanol and finally with ammonial methanol gave a compound of very low Rf on fluorescent silica eluted with ethanol. Crystallization from acetone and recrystallizations from ether-petroleum ether gave the above-titled product as colorless prisms. m.p. 142°-144°.

Workup

  1. temperatureat reflux for 48 hours
  2. customThe reaction mixture was then evaporated to a residue which
  3. washwas washed with water
  4. dissolutiondissolved in methylene chloride
  5. customchromatographed over a column of Florisil
  6. customThe first fraction yielded the recovery of 2.7 g
  7. washElution with acetone, ethanol, methanol
  8. customfinally with ammonial methanol gave a compound of very low Rf on fluorescent silica
  9. washeluted with ethanol
  10. customCrystallization
  11. customfrom acetone and recrystallizations from ether-petroleum ether

Sources & evidence

ORD record
ord-53dec5dfbfa846ebbca2c8c398ae2db8
Source dataset
uspto-grants-1976_12
Patent number
US03997591

Reaction notes

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