Piperidine → HCID 12834693, compound

HRID 354780Notes

Reaction equation

HRID 354780 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]([C:16](=[O:20])[CH2:17][CH2:18]Cl)[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[NH:9][C:10](=[O:11])[C:4]=2[CH:3]=1.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>O1CCOCC1>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]([C:16](=[O:20])[CH2:17][CH2:18][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[NH:9][C:10](=[O:11])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 20506252HCID 20506252, compound

Product 1

HCID 12834693HCID 12834693, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5.0 gm (0.015 mol) of 2-chloro-5-(3-chloropropionyl)-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one and 4.3 gm (0.05 mol) of piperidine were refluxed in 100 ml of dioxane for 1 hour. The reaction mixture was evaporated in vacuo, the residue was dissolved in dilute acetic acid, and the solution was filtered after addition of activated charcoal. The filtrate was made alkaline with ammonia and extracted with chloroform. The chloroform solution was evaporated in vacuo, and the residue was crystallized from isopropanol and recrystallized from methanol. 2.9 gm of the title compound, m.p. 170°-172° C., were obtained.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionthe residue was dissolved in dilute acetic acid
  3. filtrationthe solution was filtered
  4. additionafter addition of activated charcoal
  5. extractionextracted with chloroform
  6. customThe chloroform solution was evaporated in vacuo
  7. customthe residue was crystallized from isopropanol
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-8a30897b99404cefbf545088bcc906bf
Source dataset
uspto-grants-1983_03
Patent number
US04377576

Reaction notes

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