Hydrochloric Acid → HCID 12915185, compound

HRID 647452Notes

Reaction equation

HRID 647452 reaction equation
[ClH:1].[NH2:2][C:3]1[CH:20]=[CH:19][CH:18]=[CH:17][C:4]=1[CH2:5][CH:6]([NH:13][CH2:14][CH2:15][CH3:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:21](OCC)(OCC)(OCC)[CH3:22]>>[ClH:1].[CH3:21][C:22]1[N:13]([CH2:14][CH2:15][CH3:16])[CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][C:4]2[CH:17]=[CH:18][CH:19]=[CH:20][C:3]=2[N:2]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 66221Triethyl orthoacetateHCID 12915167HCID 12915167, compound

Product 1

HCID 12915185HCID 12915185, compound

Procedure

90 ml of Ethanolic hydrogen chloride is added dropwise to a stirred suspension of 9.00 g of 2-amino-α-phenyl-N-propylphenethylamine in 90 ml of triethyl orthoacetate. After complete addition, the mixture is refluxed for 2 hours. The ethanol is slowly distilled from the mixture and additional ethanolic hydrogen chloride (50 ml) is added. The mixture is then distilled to a volume of 20-30 ml. 100 ml of ether is added causing precipitation of the hydrochloride salt. The salt is collected, washed with ether (100 ml) and dried to give white crystals, mp 272°-275° C. of 4,5-dihydro-2-methyl-4-phenyl-3-propyl-3H-1,3-benzodiazepine hydrochloride.

Workup

  1. additionAfter complete addition
  2. temperaturethe mixture is refluxed for 2 hours
  3. distillationThe ethanol is slowly distilled from the mixture and additional ethanolic hydrogen chloride (50 ml)
  4. additionis added
  5. distillationThe mixture is then distilled to a volume of 20-30 ml
  6. addition100 ml of ether is added
  7. customprecipitation of the hydrochloride salt
  8. customThe salt is collected
  9. washwashed with ether (100 ml)
  10. customdried

Sources & evidence

ORD record
ord-e357457fbd2742ea92c643c5de727ffe
Source dataset
uspto-grants-1983_10
Patent number
US04409145

Reaction notes

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