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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 1075860
Notes
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Reaction equation

HRID 1075860 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]thiepin-10-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-417598f2acdf4a73864a17e07dbb9d6f
Source dataset
uspto-grants-1976_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03954764

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes