Ethylene Glycol → 1-(2-Bromo-10,11-dihydro-dibenzo[b,f]thiepin-10-yl)-piperazine

HRID 435697Notes

Reaction equation

HRID 435697 reaction equation
Cl.C([N:7]1[CH2:12][CH2:11][N:10]([CH:13]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[S:17][C:16]3[CH:24]=[CH:25][C:26]([Br:28])=[CH:27][C:15]=3[CH2:14]2)[CH2:9][CH2:8]1)(OCC)=O.C(O)CO.[OH-].[K+]>O>[Br:28][C:26]1[CH:25]=[CH:24][C:16]2[S:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH:13]([N:10]3[CH2:9][CH2:8][NH:7][CH2:12][CH2:11]3)[CH2:14][C:15]=2[CH:27]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 214811451-Carbethoxy-4-(2-bromo-10,11-dihydro-dibenzo[b,f]thiepin-10-yl)-piperazine hydrochloride

Product 1

HCID 214811421-(2-Bromo-10,11-dihydro-dibenzo[b,f]thiepin-10-yl)-piperazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

47.2 g of 1-carbethoxy-4-(2-bromo-10,11-dihydro-dibenzo[b,f]thiepin-10-yl)-piperazine hydrochloride, 585 ml of ethylene glycol, 32.8 g of potassium hydroxide and 1.95 ml of water are heated to 160° C for 90 minutes. Then the mixture is poured on to water and extracted with chloroform. The organic solution is extracted with 2-N hydrochloric acid. The hydrochloric acid solution is made alkaline, extracted with chloroform, washed with water, dried over magnesium sulphate and concentrated under reduced pressure. There is obtained crystalline 1-(2-bromo-10,11-dihydro-dibenzo[b,f]thiepin-10-yl)-piperazine of melting point 112°-115° C.

Workup

  1. extractionextracted with chloroform
  2. extractionThe organic solution is extracted with 2-N hydrochloric acid
  3. extractionextracted with chloroform
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-595aebf13b8c4a3eb896cd4b8319dd2f
Source dataset
uspto-grants-1977_02
Patent number
US04006144

Reaction notes

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