Acetyl chloride → HCID 4420006, compound

HRID 1389287Notes

Reaction equation

HRID 1389287 reaction equation
C(Cl)(=O)C.[C:5]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]2[C:20]3[CH:21]=[C:22]([CH:25]([CH3:27])[CH3:26])[CH:23]=[CH:24][C:19]=3[S:18][C:17]3[CH:28]=[C:29]([F:32])[CH:30]=[CH:31][C:16]=3[CH2:15]2)[CH2:10][CH2:9]1)(=O)[CH3:6]>C(Cl)(Cl)Cl>[CH2:5]([N:8]1[CH2:9][CH2:10][N:11]([CH:14]2[C:20]3[CH:21]=[C:22]([CH:25]([CH3:27])[CH3:26])[CH:23]=[CH:24][C:19]=3[S:18][C:17]3[CH:28]=[C:29]([F:32])[CH:30]=[CH:31][C:16]=3[CH2:15]2)[CH2:12][CH2:13]1)[CH3:6]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 13076189HCID 13076189, compound

Product 1

HCID 4420006HCID 4420006, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 5.0 g 3-fluoro-8-isopropyl-10-piperazine-10,11-dihydrodibenzo(b,f)thiepin in 20 ml chloroform is stirred and treated dropwise with 2.2 g acetyl chloride. The mixture is then left overnight at room temperature. Then, the separated hygroscopic hydrochloride of the product is filtered with suction, suspended in water and the base released by an excess of 20% sodium hydroxide solution and isolated by extraction with chloroform. Processing of the extract yields 5.4 g (95%) crude base of 10-(4-acetylpiperazino)-3-fluoro-8-isopropyl-10,11-dihydrodibenzo(b,f)thiepin which crystallizes from a mixture of benzene and petroleum ether and melts in a pure state at 164.5°-166° C.

Workup

  1. filtrationThen, the separated hygroscopic hydrochloride of the product is filtered with suction
  2. customisolated by extraction with chloroform

Sources & evidence

ORD record
ord-6b7624d5faa64b6bb79735d521b55bf2
Source dataset
uspto-grants-1981_01
Patent number
US04243805

Reaction notes

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