Diethylaminoethyl chloride → HCID 12291137, compound

HRID 1579067Notes

Reaction equation

HRID 1579067 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:15]4[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=4[CH2:13][CH2:12][C:11]=3[C:10]([C:21]([OH:23])=[O:22])=[N:9]2)=[CH:4][CH:3]=1.[CH2:24]([N:26]([CH2:30][CH3:31])[CH2:27][CH2:28]Cl)[CH3:25]>CC(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:15]4[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=4[CH2:13][CH2:12][C:11]=3[C:10]([C:21]([O:23][CH2:25][CH2:24][N:26]([CH2:30][CH3:31])[CH2:27][CH3:28])=[O:22])=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 13364Diethylaminoethyl chlorideHCID 12291085HCID 12291085, compound

Product 1

HCID 12291137HCID 12291137, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 10 parts of 1-(4-chlorophenyl)-4,5-dihydro-1H-benz[g]indazole-3-carboxylic acid, 5parts of 2-diethylaminoethyl chloride and 160 parts of anhydrous 2-propanol is heated at reflux for 16 hours. The 2-propanol is then removed under reduced pressure and the resulting residue is partitioned in ether and dilute hydrochloric acid. The aqueous layer is separated and washed twice with ether. It is then made alkaline with cold aqueous sodium hydroxide solution and then extracted with ether. The combined ether extracts are dried over potassium carbonate and the solvent is evaporated to leave a residual free base. This is recrystallized from a mixture of benzene and hexane to give 2-diethylaminoethyl 1-(4-chlorophenyl)-4,5-dihydro-1H-benz[g]indazole-3-carboxylate melting at about 102°-103°C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 16 hours
  3. customThe 2-propanol is then removed under reduced pressure
  4. customthe resulting residue is partitioned in ether
  5. customThe aqueous layer is separated
  6. washwashed twice with ether
  7. extractionextracted with ether
  8. dry with materialThe combined ether extracts are dried over potassium carbonate
  9. customthe solvent is evaporated
  10. customto leave a residual free base
  11. customThis is recrystallized from a mixture of benzene and hexane

Sources & evidence

ORD record
ord-37bbb880b54a473f9d8417ba7dca9e3a
Source dataset
uspto-grants-1976_02
Patent number
US03940418

Reaction notes

Loading…