Dicyclohexylcarbodiimide → Monatepil

HRID 579752Notes

Reaction equation

HRID 579752 reaction equation
[NH2:1][CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][S:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2.[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][CH2:32][C:33](O)=[O:34])[CH2:26][CH2:25]2)=[CH:20][CH:19]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[F:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[CH2:25][CH2:26][N:27]([CH2:30][CH2:31][CH2:32][C:33]([NH:1][CH:2]3[C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=4[CH2:6][S:5][C:4]4[CH:13]=[CH:14][CH:15]=[CH:16][C:3]3=4)=[O:34])[CH2:28][CH2:29]2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 124891006,11-Dihydrodibenzo[b,e]thiepin-11-amineHCID 14879738HCID 14879738, compound

Product 1

HCID 60810MonatepilYield 39.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.3 g of 11-amino-6,11-dihydrodibenzo[b,e]thiepin, 2.9 g of 4-[4-(4-fluorophenyl)-1-piperazinyl]butyric acid, 2.3 g of dicyclohexylcarbodiimide and 50 ml of methylene chloride is stirred at room temperature for 15 hours. After removal of the precipitated crystals by filtration, the filtrate is concentrated under reduced pressure. The residue is recrystallized from chloroform-n-hexane to give 1.9 g of the title compound, m.p. 194°-194.5° C.;

Workup

  1. customAfter removal of the precipitated crystals
  2. filtrationby filtration
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe residue is recrystallized from chloroform-n-hexane

Sources & evidence

ORD record
ord-5a692d50d4ca4b8da4c1809b5a6c6644
Source dataset
uspto-grants-1988_06
Patent number
US04749703

Reaction notes

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