1-Methylpiperazine → HCID 3045477, compound

HRID 1732767Notes

Reaction equation

HRID 1732767 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Cl:8][C:9]1[C:24]([F:25])=[CH:23][C:12]2[C:13](=O)[CH2:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[S:17][C:11]=2[CH:10]=1>C1C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[Cl:8][C:9]1[C:24]([F:25])=[CH:23][C:12]2[C:13]([N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[CH:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[S:17][C:11]=2[CH:10]=1

Participants

5

Reactant 2

HCID 531671-MethylpiperazineHCID 12271952HCID 12271952, compound

Product 1

HCID 3045477HCID 3045477, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 241BenzeneSolvent2×

Procedure

1-Methylpiperazine (18.2 ml) was added to a solution of 7-chloro-8-fluorodibenzo(b,f)thiepine-10(11H)-one (see Example 24) (10.16 g) in benzene (90 ml). To this mixture a solution of titanium tetrachloride (3.7 g) in benzene (30 ml) was added dropwise during 5 minutes. The mixture was refluxed for 24 hours, cooled and decomposed by addition of ice-cold water (150 ml). After 30 minutes' standing, the precipitated solid was filtered and washed with benzene. The aqueous layer of the filtrate was extracted with the same solvent, the benzene layers combined, washed with water, dried and taken down, leaving 12.1 g (91%) of the oily base which slowly crystallizes from ethanol. When pure, it melts at 158°-160° C. Neutralization with maleic acid in ethanol yielded the crystalline maleate, m.p. 228°-230° C. (aqueous ethanol).

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. temperaturecooled
  3. filtrationthe precipitated solid was filtered
  4. washwashed with benzene
  5. extractionThe aqueous layer of the filtrate was extracted with the same solvent
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-3a494013ac594046a3c7c2bc5c3ffb77
Source dataset
uspto-grants-1980_12
Patent number
US04238611

Reaction notes

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