Ethylene Glycol → 1-(3-Chloro-5,6-dihydrobenzo[b][1]benzothiepin-6-yl)piperazine

HRID 435674Notes

Reaction equation

HRID 435674 reaction equation
C([N:6]1[CH2:11][CH2:10][N:9]([CH:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[S:16][C:15]3[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:14]=3[CH2:13]2)[CH2:8][CH2:7]1)(OCC)=O.C(O)CO.[OH-].[K+]>O>[Cl:27][C:25]1[CH:24]=[CH:23][C:15]2[S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH:12]([N:9]3[CH2:8][CH2:7][NH:6][CH2:11][CH2:10]3)[CH2:13][C:14]=2[CH:26]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 12947376HCID 12947376, compound

Product 1

HCID 30559791-(3-Chloro-5,6-dihydrobenzo[b][1]benzothiepin-6-yl)piperazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

110 g of 1-carbethoxy-4-(2-chloro-10,11-dihydro-dibenzo[b,f]thiepin-10-yl)-piperazine, 1.5 litres of ethylene glycol, 104 g of potassium hydroxide and 5.4 ml of water are heated to 160° C for 1 hour. The mixture is then poured on to water and extracted with chloroform. The organic phase is washed with water, dried over magnesium sulphate and evaporated. There is obtained 1-(2-chloro-10,11-dihydro-dibenzo[b,f]thiepin-10-yl)-piperazine as an oil.

Workup

  1. extractionextracted with chloroform
  2. washThe organic phase is washed with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-e3167d9ceb9c4978a9b8965235c6641c
Source dataset
uspto-grants-1977_02
Patent number
US04006144

Reaction notes

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