Sodium Iodide → 1-{2-[4-(10,11-Dihydro-3-methoxy-8-methylthio-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-pyrrolidinone

HRID 1075875Notes

Reaction equation

HRID 1075875 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH:11]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[C:10]3[CH:19]=[C:20]([S:23][CH3:24])[CH:21]=[CH:22][C:9]=3[S:8][C:7]=2[CH:25]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl[CH2:35][CH2:36][N:37]1[CH2:41][CH2:40][CH2:39][C:38]1=[O:42]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH:11]([N:13]3[CH2:14][CH2:15][N:16]([CH2:35][CH2:36][N:37]4[CH2:41][CH2:40][CH2:39][C:38]4=[O:42])[CH2:17][CH2:18]3)[C:10]3[CH:19]=[C:20]([S:23][CH3:24])[CH:21]=[CH:22][C:9]=3[S:8][C:7]=2[CH:25]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 31566501-(2-Chloroethyl)pyrrolidin-2-oneHCID 134982451-(10,11-Dihydro-3-methoxy-8-methylthio-dibenzo[b,f]thiepin-10-yl)-piperazine

Product 1

HCID 214162011-{2-[4-(10,11-Dihydro-3-methoxy-8-methylthio-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-pyrrolidinone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

11 G. of 1-(10,11-dihydro-3-methoxy-8-methylthio-dibenzo[b,f]thiepin-10-yl)-piperazine are heated together with 15 g. of potassium carbonate, 0.5 g. of sodium iodide, 11 g. of N-(β-chloroethyl)-2-pyrrolidinone and 100 ml. of toluene under reflux conditions for 17 hours. Then, the mixture is evaporated under reduced pressure. The residue is partitioned between water and ether, and the ethereal phase dried over sodium sulfate and evaporated. The residue obtained is chromatographed with chloroform over aluminum oxide. The 1-{2-[4-(10,11-dihydro-3-methoxy-8-methylthio-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-pyrrolidinone thus obtained is converted into the corresponding dihydrochloride by reaction with hydrogen chloride. The resulting dihydrochloride melts at 202°C.

Workup

  1. customThen, the mixture is evaporated under reduced pressure
  2. customThe residue is partitioned between water and ether
  3. dry with materialthe ethereal phase dried over sodium sulfate
  4. customevaporated
  5. customThe residue obtained
  6. customis chromatographed with chloroform over aluminum oxide

Sources & evidence

ORD record
ord-4ce7f1fc5d7647a9aac5fd9517c262b8
Source dataset
uspto-grants-1976_05
Patent number
US03954764

Reaction notes

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