Triethylamine → HCID 70637795, compound

HRID 1581016Notes

Reaction equation

HRID 1581016 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:12][Cl:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)[CH:28]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH:31]1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH3:29])C.[CH2:44]([N:46](CC)[CH2:47][CH3:48])[CH3:45]>CC(CC)=O>[ClH:13].[CH2:44]([N:46]([CH2:29][CH2:28][N:30]1[CH2:35][CH2:34][N:33]([CH2:12][C:11]2[CH:14]=[CH:15][C:16]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:10]=2)[CH2:32][CH:31]1[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[CH2:47][CH3:48])[CH3:45]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 743393,5-Bis(benzyloxy)-alpha-chlorotolueneHCID 21448529HCID 21448529, compound

Product 1

HCID 70637795HCID 70637795, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

30 g. of 3,4-dibenzyloxy benzylchloride, 23 g. of 1-diethylamino ethyl-2-phenyl piperazine, 20 ml. of triethylamine, and 200 ml. of methylethylketone are boiled under reflux for 12 hours. The precipitated triethylamine hydrochloride is filtered off by suction. The solvent is distilled off and the residue is dissolved in benzene. The benzene solution is extracted with dilute hydrochloric acid (1 : 8). The hydrochloric acid extract is rendered alkaline by the addition of ammonia and is extracted with benzene. The benzene is removed from the benzene extract by distillation. Water-free alcoholic hydrochloric acid is added to the residue, and the hydrochloride of the resulting base is precipitated by the addition of a mixture of petroleum ether and acetone (1 : 1). The hydrochloride is redissolved in alcohol and is again precipitated by the addition of petroleum ether and acetone. Melting point of the hydrochloride: It starts to sublimate at 203° C. and melts at 235°-239° C. with decomposition. White crystals.

Workup

  1. temperatureunder reflux for 12 hours
  2. filtrationThe precipitated triethylamine hydrochloride is filtered off by suction
  3. distillationThe solvent is distilled off
  4. dissolutionthe residue is dissolved in benzene
  5. extractionThe benzene solution is extracted with dilute hydrochloric acid (1 : 8)
  6. extractionThe hydrochloric acid extract
  7. additionby the addition of ammonia
  8. extractionis extracted with benzene
  9. customThe benzene is removed from the benzene
  10. extractionextract by distillation
  11. additionWater-free alcoholic hydrochloric acid is added to the residue
  12. customthe hydrochloride of the resulting base is precipitated by the addition of a mixture of petroleum ether and acetone (1 : 1)
  13. dissolutionThe hydrochloride is redissolved in alcohol
  14. customis again precipitated by the addition of petroleum ether and acetone
  15. customto sublimate at 203° C.

Sources & evidence

ORD record
ord-5df37a24199742e4926dfe1ae93f26d7
Source dataset
uspto-grants-1976_01
Patent number
US03935214

Reaction notes

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