Acetic Anhydride → 2-[4-(9-Fluoro-3-propan-2-yl-5,6-dihydrobenzo[b][1]benzothiepin-5-yl)piperazin-1-yl]ethyl acetate

HRID 1389291Notes

Reaction equation

HRID 1389291 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH:10]([N:12]3[CH2:17][CH2:16][N:15]([CH2:18][CH2:19]CO)[CH2:14][CH2:13]3)[C:9]3[CH:22]=[C:23]([CH:26]([CH3:28])[CH3:27])[CH:24]=[CH:25][C:8]=3[S:7][C:6]=2[CH:29]=1.[C:30]([O:33]C(=O)C)(=[O:32])[CH3:31]>C(Cl)(Cl)Cl>[C:30]([O:33][CH2:19][CH2:18][N:15]1[CH2:14][CH2:13][N:12]([CH:10]2[C:9]3[CH:22]=[C:23]([CH:26]([CH3:27])[CH3:28])[CH:24]=[CH:25][C:8]=3[S:7][C:6]3[CH:29]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[CH2:11]2)[CH2:17][CH2:16]1)(=[O:32])[CH3:31]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 130761743-Fluoro-10-[4-(3-hydroxypropyl)piperazino]-8-isopropyl-10,11-dihydrodibenzo (b,f) thiepin

Product 1

HCID 34324762-[4-(9-Fluoro-3-propan-2-yl-5,6-dihydrobenzo[b][1]benzothiepin-5-yl)piperazin-1-yl]ethyl acetate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 1.0 g of 3-fluoro-10-[4-(2-hydroxyethyl)piperazino]-8-isopropyl-10,11-dihydrodibenzo(b,f)thiepin base (Example 3) in 5 ml chloroform was treated with 0.5 g acetic anhydride and the mixture allowed to stand overnight at room temperature. It was then diluted with 20 ml of chloroform, washed with water and with ice-cold sodium hydroxide solution, dried with potassium carbonate, and the chloroform evaporated under reduced pressure. The remaining oil (1.1 g, 100%) was dissolved in 3.5 ml of acetone and the solution neutralized under heating with 0.6 g maleic acid. On cooling, 1.3 g (77%) of dimaleate crystallized which was then recrystallized from acetone and melted at 153°-155.5° C.; it was identical with the product obtained by a different way according to Example 14.

Workup

  1. washwashed with water and with ice-cold sodium hydroxide solution
  2. dry with materialdried with potassium carbonate
  3. customthe chloroform evaporated under reduced pressure
  4. dissolutionThe remaining oil (1.1 g, 100%) was dissolved in 3.5 ml of acetone
  5. temperatureunder heating with 0.6 g maleic acid
  6. temperatureOn cooling
  7. custom1.3 g (77%) of dimaleate crystallized which
  8. customwas then recrystallized from acetone and melted at 153°-155.5° C.
  9. customobtained by a different way

Sources & evidence

ORD record
ord-6bd7e88873374ee08175ae3f9d5e85c4
Source dataset
uspto-grants-1981_01
Patent number
US04243805

Reaction notes

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