1-Methylpiperazine → 9-(4-Methyl-piperazin-1-yl)-4-thia-10a-aza-benzo[f]azulene

HRID 49755Notes

Reaction equation

HRID 49755 reaction equation
[CH:1]1[N:10]2[C:4]([S:5][C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[C:8](=O)[CH2:9]2)=[CH:3][CH:2]=1.[CH3:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.O([Si](C)(C)C)S(C(F)(F)F)(=O)=O>O>[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([C:8]2[C:7]3[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=3[S:5][C:4]3=[CH:3][CH:2]=[CH:1][N:10]3[CH:9]=2)[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 531671-Methylpiperazine2×HCID 65367Trimethylsilyl triflateHCID 108225689,10-Dihydropyrrolo[2,1-b][1,3]benzothiazepin-9-one

Product 1

HCID 97962559-(4-Methyl-piperazin-1-yl)-4-thia-10a-aza-benzo[f]azuleneYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 9,10-dihydropyrrolo[2,1-b][1,3]benzothiazepin-9-one (0.24 g, 1.11 mmol), N-methylpiperazine (0.55 mL, 0.50 g, 4.99 mmol) and trimethylsilyl triflate (0.55 mL, 0.68 g, 3.05 mmol) was heated at 120° C. under stirring, after a few minutes further 0.55 mL of N-methylpiperazine were added and the reaction was kept for 3 hours at 120° C. After that time water was added and was extracted with dichloromethane. The organic layer was dried over sodium sulphate, filtered and evaporated to give the crude product that was purified by means of a flash chromatography (20% methanol in ethyl acetate) to afford 0.114 g of the pure title compound as a yellowish solid (84% yield).

Workup

  1. additionwere added
  2. extractionwas extracted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customto give the crude product that
  7. customwas purified by means of a flash chromatography (20% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-839aa6d361804ea2a67fc94a608c6737
Source dataset
uspto-grants-2004_03
Patent number
US06710041B2

Reaction notes

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