1-Methylpiperazine → HCID 3045791, compound

HRID 1732768Notes

Reaction equation

HRID 1732768 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[C:18]([Cl:19])=[CH:17][C:6]2[CH:7](Cl)[CH2:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[S:11][C:5]=2[CH:4]=1.[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>C(Cl)(Cl)Cl>[F:1][C:2]([F:21])([F:20])[C:3]1[C:18]([Cl:19])=[CH:17][C:6]2[CH:7]([N:26]3[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]3)[CH2:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[S:11][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 12374624HCID 12374624, compound

Product 1

HCID 3045791HCID 3045791, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 7-trifluoromethyl-8,10-dichloro-10,11-dihydrodibenzo(b,f)thiepine (2.89 g), 1-methylpiperazine (1.8 ml) and chloroform (2.5 ml) was refluxed for 7 hours. The chloroform was evaporated under diminished pressure, the residue dissolved in benzene (30 ml), washed with water, and the benzene layer separated and shaken with an excess of 3 N-HCl. The precipitated hydrochloride was filtered, added to the aqueous layer of the filtrate and the base liberated by addition of ammonium hydroxide. It was extracted with benzene and the conventional work-up procedure yielded 1.93 g (56%) of the crude 7-trifluoromethyl-8-chloro-10-(4-methylpiperazino)-10,11-dihydrodibenzo(b,f)thiepine. Neutralization with maleic acid in ethanol followed by addition of ether yielded the crystalline maleate which was crystallized from ethanol; m.p. 197°-200° C.

Workup

  1. temperaturewas refluxed for 7 hours
  2. customThe chloroform was evaporated under diminished pressure
  3. dissolutionthe residue dissolved in benzene (30 ml)
  4. washwashed with water
  5. customthe benzene layer separated
  6. filtrationThe precipitated hydrochloride was filtered
  7. additionadded to the aqueous layer of the filtrate
  8. additionthe base liberated by addition of ammonium hydroxide
  9. extractionIt was extracted with benzene

Sources & evidence

ORD record
ord-935a7a3f8ffd43babf405a333effcddc
Source dataset
uspto-grants-1980_12
Patent number
US04238611

Reaction notes

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