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1-Piperazinecarboxylic acid, ethyl ester → 1-Carbethoxy-4-(8-chloro-2-methyl-dibenzo[b,f]thiepin-10-yl)-piperazine

HRID 441979
Notes
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Reaction equation

HRID 441979 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:9]=3[CH2:8][C:7](=O)[C:6]=2[CH:18]=1.[C:19]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)([O:21][CH2:22][CH3:23])=[O:20].C(=O)(O)[O-].[Na+]>[Ti](Cl)(Cl)(Cl)Cl.C1C=CC=CC=1>[C:19]([N:24]1[CH2:29][CH2:28][N:27]([C:7]2[C:6]3[CH:18]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[S:11][C:10]3[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:9]=3[CH:8]=2)[CH2:26][CH2:25]1)([O:21][CH2:22][CH3:23])=[O:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 516892Sodium BicarbonateHCID 214160928-chloro-2-methyl-dibenzo[b,f]thiepin-10(11H)-one

Product 1

HCID 214161321-Carbethoxy-4-(8-chloro-2-methyl-dibenzo[b,f]thiepin-10-yl)-piperazine

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalyst
HCID 241BenzeneSolvent2×

Procedure

111.4 G. of 8-chloro-2-methyl-dibenzo[b,f]thiepin-10(11H)-one in 1 l. of absolute benzene are mixed together with 268 ml. of carbethoxypiperazine and within 1 hour at 20°-25° with a solution of 65 ml. of titanium tetrachloride in 500 ml. of absolute benzene. The resulting reaction mixture thereafter is heated under reflux conditions over a period of 20 hours. The reaction mixture is then poured over a mixture of 500 ml. of saturated aqueous sodium bicarbonate solution and 700 ml. of water with strong stirring, subsequently filtered, and washed again with chloroform. After an equilibrium is reached between both phases, the organic phase is dried and evaporated, whereby there is obtained 1-carbethoxy-4-(8-chloro-2-methyl-dibenzo[b,f]thiepin-10-yl)-piperazine as a dark brown viscous oil.

Workup

  1. customThe resulting reaction mixture
  2. temperaturethereafter is heated under reflux conditions over a period of 20 hours
  3. additionThe reaction mixture is then poured over a mixture of 500 ml
  4. filtrationof water with strong stirring, subsequently filtered
  5. washwashed again with chloroform
  6. customthe organic phase is dried
  7. customevaporated

Sources & evidence

ORD record
ord-e02dae08cf284ece8132a1469e08e219
Source dataset
uspto-grants-1977_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04044010

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes