N,N-Diethylethylenediamine → HCID 12291098, compound

HRID 1579065Notes

Reaction equation

HRID 1579065 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:13]3[N:12]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[N:11]=[C:10]([C:20](OC)=[O:21])[C:9]=3[CH2:8][CH2:7][C:6]=2[CH:24]=1.[CH2:25]([N:27]([CH2:31][CH3:32])[CH2:28][CH2:29][NH2:30])[CH3:26]>>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:13]3[N:12]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:11]=[C:10]([C:20]([NH:30][CH2:29][CH2:28][N:27]([CH2:31][CH3:32])[CH2:25][CH3:26])=[O:21])[C:9]=3[CH2:8][CH2:7][C:6]=2[CH:24]=1

Participants

3

Reactant 2

HCID 60993N,N-DiethylethylenediamineHCID 12291071HCID 12291071, compound

Product 1

HCID 12291098HCID 12291098, compound

Procedure

A mixture of 5 parts of methyl 7-chloro-1-phenyl-4,5-dihydro-1H-benz[g]indazole-3-carboxylate and 40 parts of 2-diethylaminoethylamine is heated at reflux for 3 hours. Excess amine is distilled off under reduced pressure and the reside is partitioned in ether and dilute aqueous hydrochloric acid. The aqueous layer is then separated and washed twice with ether and it is made alkaline with an aqueous sodium hydroxide solution. The resulting mixture is then extracted with ether and the ether extracts are dried over potassium carbonate. The ether solvent is removed under reduced pressure, the resulting oil is dissolved in anhydrous ethanol, and a slight excess of hydrogen chloride in 2-propanol is added. Anhydrous ether is then added until the mixture becomes turbid, and the mixture is cooled. The solid which forms is separated by filtration and recrystallized from a mixture of ethanol and ether to give 7-chloro-N-(2-diethylaminoethyl)-1-phenyl-4,5-dihydro-1H-benz[g]indazole-3-carboxamide hydrochloride melting at about 229°-231°C. The free base of this compound has the following formula ##SPC3##

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3 hours
  3. distillationExcess amine is distilled off under reduced pressure
  4. customthe reside is partitioned in ether
  5. customThe aqueous layer is then separated
  6. washwashed twice with ether and it
  7. extractionThe resulting mixture is then extracted with ether
  8. dry with materialthe ether extracts are dried over potassium carbonate
  9. customThe ether solvent is removed under reduced pressure
  10. dissolutionthe resulting oil is dissolved in anhydrous ethanol
  11. additiona slight excess of hydrogen chloride in 2-propanol is added
  12. additionAnhydrous ether is then added until the mixture
  13. temperaturethe mixture is cooled
  14. customThe solid which forms is separated by filtration
  15. customrecrystallized from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-b8c1adc521d04dfca9bf03954b126f64
Source dataset
uspto-grants-1976_02
Patent number
US03940418

Reaction notes

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