Piperidine → HCID 20355332, compound

HRID 1605906Notes

Reaction equation

HRID 1605906 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 reduce 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
  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-cdcd9543f68746ed8f5f199c26087641
Source dataset
uspto-grants-1976_04
Patent number
US03951981

Reaction notes

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