Ethylene Glycol → 1-(8-Chloro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)piperazine

HRID 1075863Notes

Reaction equation

HRID 1075863 reaction equation
C([N:6]1[CH2:11][CH2:10][N:9]([CH:12]2[C:18]3[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=3[S:16][C:15]3[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:14]=3[CH2:13]2)[CH2:8][CH2:7]1)(OCC)=O.C(O)CO.[OH-].[K+]>O>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]2[S:16][C:15]3[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:14]=3[CH2:13][CH:12]([N:9]3[CH2:10][CH2:11][NH:6][CH2:7][CH2:8]3)[C:18]=2[CH:19]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 214160911-Carbethoxy-4-(8-chloro-10,11-dihydro-2-methyl-dibenzo[b,f]-thiepin-10-yl)piperazine

Product 1

HCID 214161631-(8-Chloro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)piperazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

95 G. of 1-carbethoxy-4-(8-chloro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)-piperazine are stirred together with 1,000 ml. of ethyleneglycol, 77 g. of potassium hydroxide and 10 ml. of water on a bath of 160° for 6 hours. The reaction mixture is poured over ice water and extracted with ether. The ether extract is washed with water, dried and evaporated, whereby 1-(8-chloro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)-piperazine is obtained as a red-brown viscous oil. After recrystallization from acetone/petroleum ether the product is obtained as crystals having a melting point of 125°-127°.

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washis washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-9853a00cdee74ed5a7f4d1b25ce25f3e
Source dataset
uspto-grants-1976_05
Patent number
US03954764

Reaction notes

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