N-Ethylbenzylamine → 5-[3-(N-Benzyl-N-ethylamino)-propyl]-5H-dibenzo[a,d]cycloheptene

HRID 2071730Notes

Reaction equation

HRID 2071730 reaction equation
I[CH2:2][CH2:3][CH2:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[CH:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2.[CH2:20]([NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH3:21]>>[CH2:23]([N:22]([CH2:2][CH2:3][CH2:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[CH:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2)[CH2:20][CH3:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 84352N-EthylbenzylamineHCID 233288685-(3-iodopropyl)-5H-dibenzo[a,d]cycloheptene

Product 1

HCID 214121395-[3-(N-Benzyl-N-ethylamino)-propyl]-5H-dibenzo[a,d]cycloheptene

Procedure

5-(3-Iodopropyl)-5H-dibenzo[a,d]cycloheptene is added gradually to an excess of N-ethyl benzylamine in absolute alcohol with stirring and cooling. The reaction mixture then is heated to refluxing for 30 minutes and the alcohol distilled under reduced pressure. The residue is warmed with dilute acid and the acid-insoluble material separated. The aqueous layer then is rendered alkaline with sodium hydroxide and the liberated bases extracted into ether. The ether is evaporated and the product isolated by vacuum distillation.

Workup

  1. temperaturecooling
  2. temperatureThe reaction mixture then is heated
  3. temperatureto refluxing for 30 minutes
  4. distillationthe alcohol distilled under reduced pressure
  5. temperatureThe residue is warmed
  6. additionwith dilute acid
  7. customthe acid-insoluble material separated
  8. extractionthe liberated bases extracted into ether
  9. customThe ether is evaporated
  10. customthe product isolated by vacuum distillation

Sources & evidence

ORD record
ord-862c50f2c2ff4b34a34e38749b3eff03
Source dataset
uspto-grants-1977_09
Patent number
US04048223

Reaction notes

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