Piperidine → HCID 20355332, compound

HRID 371630Notes

Reaction equation

HRID 371630 reaction equation
CS[C:3]1[C:4]2[C:5](=[CH:14][S:15][CH:16]=2)[NH:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1.[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>C(O)(=O)C>[N:17]1([C:3]2[C:4]3[C:5](=[CH:14][S:15][CH:16]=3)[NH:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[N:9]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 12521659HCID 12521659, compound

Product 1

HCID 20355332HCID 20355332, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 0.7 g. of 10-(methylthio)-4H-thieno[3,4-b][1,5]benzodiazepine in 5 ml. of piperidine is treated with a drop of glacial acetic acid and heated under reflux for 4 days. Excess piperidine is removed under reduced pressure and the oily residue is warmed with dilute acetic acid and filtered. The filtrate is cooled and made alkaline with concentrated ammonium hydroxide to give a yellow solid. Recrystallization from acetone-petroleum ether (30°-60° C.) gives yellow crystals, m.p. 157°-159° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 days
  3. customExcess piperidine is removed under reduced pressure
  4. temperaturethe oily residue is warmed with dilute acetic acid
  5. filtrationfiltered
  6. temperatureThe filtrate is cooled
  7. customto give a yellow solid
  8. customRecrystallization from acetone-petroleum ether (30°-60° C.)
  9. customgives yellow crystals, m.p. 157°-159° C.

Sources & evidence

ORD record
ord-9c695e7f3cd84a738af83c6aef486f97
Source dataset
uspto-grants-1978_05
Patent number
US04087421

Reaction notes

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