Water → HCID 12374630, compound

HRID 1732770Notes

Reaction equation

HRID 1732770 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[F:8][C:9]([F:28])([F:27])[C:10]1[C:25]([Cl:26])=[CH:24][C:13]2[C:14](=O)[CH2:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[S:18][C:12]=2[CH:11]=1.O>C1C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[F:8][C:9]([F:28])([F:27])[C:10]1[C:25]([Cl:26])=[CH:24][C:13]2[C:14]([N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[CH:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[S:18][C:12]=2[CH:11]=1

Participants

6

Reactant 3

HCID 962WaterHCID 531671-MethylpiperazineHCID 12374616HCID 12374616, compound

Product 1

HCID 12374630HCID 12374630, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 241BenzeneSolvent2×

Procedure

1-Methylpiperazine (8.0 g) was added to a solution of 7-trifluoromethyl-8-chlorodibenzo(b,f)thiepine-10(11H)-one (the preparation of which is described in the preceding Example) (5.17 g) in benzene (40 ml). Then, titanium tetrachloride (1.63 g) in benzene (10 ml) was added dropwise, the mixture refluxed for 24 hours while stirring, cooled and decomposed with water (60 ml). The separated solid was filtered and washed with benzene and water. The benzene layer of the filtrate was separated, washed with water, filtered with charcoal and dried over magnesium sulfate. Evaporation of the benzene yielded 5.68 g (88%) of the crude enamine base, named in the heading of this Example. Neutralization of this base with methanesulfonic acid in ethanol, followed by addition of ether, yielded the crystalline methanesulfonate which crystallized from acetone as a monohydrate; m.p. 267°-270° C.

Workup

  1. customthe preparation of which
  2. temperaturethe mixture refluxed for 24 hours
  3. temperaturecooled
  4. filtrationThe separated solid was filtered
  5. washwashed with benzene and water
  6. customThe benzene layer of the filtrate was separated
  7. washwashed with water
  8. filtrationfiltered with charcoal
  9. dry with materialdried over magnesium sulfate
  10. customEvaporation of the benzene

Sources & evidence

ORD record
ord-0c200465a90d4645a1578f5326e261b3
Source dataset
uspto-grants-1980_12
Patent number
US04238611

Reaction notes

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