1-Methylpiperazine → HCID 12271965, compound

HRID 1732760Notes

Reaction equation

HRID 1732760 reaction equation
[F:1][C:2]1[C:17]([F:18])=[CH:16][C:5]2[CH:6](Cl)[CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[S:10][C:4]=2[CH:3]=1.[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>C(Cl)(Cl)Cl>[F:1][C:2]1[C:17]([F:18])=[CH:16][C:5]2[CH:6]([N:23]3[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]3)[CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[S:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 12271962HCID 12271962, compound

Product 1

HCID 12271965HCID 12271965, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 7,8-difluoro-10-chloro-10,11-dihydrodibenzo(b,f)thiepine (5.08 g), 1-methylpiperazine (4 ml) and chloroform (5 ml) was refluxed for 7 hours. Chloroform was evaporated and the residue shaken with water and benzene. The organic layer was washed with water and shaken with dilute (1:2) hydrochlorid acid (50 ml). The formed suspension was filtered and the thus-obtained solid hydrochloride added to the aqueous layer of the filtrate. Addition of 15% sodium hydroxide solution liberated the desired base which was extracted with benzene, m.p. 106°-108° C. (acetone). Neutralization of this base with methanesulfonic or maleic acid in ethanol, followed by the addition of ether, yields the corresponding salts, i.e., the methanesulfonate (m.p. 244°-247° C.) or maleate (hemihydrate, m.p. 161°-163° C.), which were purified by crystallization from a mixture of ethanol and ether.

Workup

  1. temperaturewas refluxed for 7 hours
  2. customChloroform was evaporated
  3. washThe organic layer was washed with water
  4. stirringshaken
  5. additionwith dilute (1:2) hydrochlorid acid (50 ml)
  6. filtrationThe formed suspension was filtered
  7. additionthe thus-obtained solid hydrochloride added to the aqueous layer of the filtrate
  8. additionAddition of 15% sodium hydroxide solution
  9. extractionwas extracted with benzene, m.p. 106°-108° C. (acetone)
  10. additionNeutralization of this base with methanesulfonic or maleic acid in ethanol, followed by the addition of ether
  11. customyields the corresponding salts, i.e.
  12. customthe methanesulfonate (m.p. 244°-247° C.) or maleate (hemihydrate, m.p. 161°-163° C.), which were purified by crystallization from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-a134fd5308564eaf8390f077e34bebbe
Source dataset
uspto-grants-1980_12
Patent number
US04238611

Reaction notes

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