1-Piperazinecarboxylic acid, ethyl ester → 1-(9-Fluoro-3-propan-2-yl-5,6-dihydrobenzo[b][1]benzothiepin-5-yl)piperazine

HRID 1389290Notes

Reaction equation

HRID 1389290 reaction equation
Cl[CH:2]1[C:8]2[CH:9]=[C:10]([CH:13]([CH3:15])[CH3:14])[CH:11]=[CH:12][C:7]=2[S:6][C:5]2[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:4]=2[CH2:3]1.C(OC([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)=O)C>C(Cl)(Cl)Cl>[F:20][C:17]1[CH:18]=[CH:19][C:4]2[CH2:3][CH:2]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[C:8]3[CH:9]=[C:10]([CH:13]([CH3:15])[CH3:14])[CH:11]=[CH:12][C:7]=3[S:6][C:5]=2[CH:16]=1

Participants

4

Reactant 2

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 1305067810-Chloro-3-fluoro-8-isopropyl-10,11-dihydrodibenzo(b,f)thiepin

Product 1

HCID 41250111-(9-Fluoro-3-propan-2-yl-5,6-dihydrobenzo[b][1]benzothiepin-5-yl)piperazine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A mixture of 20 g of 10-chloro-3-fluoro-8-isopropyl-10,11-dihydrodibenzo(b,f)thiepin, 21 g of 1-(ethoxycarbonyl)piperazine and 30 ml of chloroform is refluxed for 5 hours. After cooling, it is diluted with chloroform, the solution thoroughly washed with water, dried with potassium carbonate and after filtration evaporated under reduced pressure. The residue (27 g, 96%) is a crude glassy 10-(ethoxycarbonylpiperazino)-3-fluoro-8-isopropyl-10,11-dihydrodibenzo(b,f)thiepin which is used for hydrolysis in this state without further purification.

Workup

  1. temperatureis refluxed for 5 hours
  2. temperatureAfter cooling
  3. washthe solution thoroughly washed with water
  4. dry with materialdried with potassium carbonate
  5. filtrationafter filtration
  6. customevaporated under reduced pressure
  7. customis used for hydrolysis in this state without further purification

Sources & evidence

ORD record
ord-683fbb31235b43b181c674c1fa34ce0b
Source dataset
uspto-grants-1981_01
Patent number
US04243805

Reaction notes

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