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Sodium Iodide → 1-{2-[4-(8-Chloro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)1-piperazinyl]-ethyl}-2-pyrrolidinone

HRID 441978
Notes
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Reaction equation

HRID 441978 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][CH:7]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:6]=2[CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl[CH2:33][CH2:34][N:35]1[CH2:39][CH2:38][CH2:37][C:36]1=[O:40]>C1(C)C=CC=CC=1>[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][CH:7]([N:17]3[CH2:22][CH2:21][N:20]([CH2:33][CH2:34][N:35]4[CH2:39][CH2:38][CH2:37][C:36]4=[O:40])[CH2:19][CH2:18]3)[C:6]=2[CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 31566501-(2-Chloroethyl)pyrrolidin-2-oneHCID 214161631-(8-Chloro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)piperazine

Product 1

HCID 214161651-{2-[4-(8-Chloro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)1-piperazinyl]-ethyl}-2-pyrrolidinone

Reagents, catalysts & solvents

1
HCID 1140TolueneSolvent

Procedure

11 G. of 1-(8-chloro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)piperazine are heated together with 15.5 g. of potassium carbonate, 0.5 g. of sodium iodide, 11 g. of N-(beta-chloroethyl)-pyrrolidinone and 150 ml. of toluene under reflux conditions over a period of 12 hours. The reaction mixture is evaporated under reduced pressure. The residue is dispersed between water and ether and the ethereal phase is dried over sodium sulfate and evaporated, whereby there is obtained 1-{-2-[4-(8-chloro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin10-yl)-1-piperazinyl]-ethyl}-2-pyrrolidinone, having a melting point of 153°-164°. The maleate melts at 179°-180°.

Workup

  1. customThe reaction mixture is evaporated under reduced pressure
  2. additionThe residue is dispersed between water and ether
  3. dry with materialthe ethereal phase is dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-42eeaf7efd464af4bd758a1d694110be
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