Dicyclohexylcarbodiimide → HCID 20563557, compound

HRID 1154946Notes

Reaction equation

HRID 1154946 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[CH2:13][CH2:14][C:15](=[O:21])[NH:16]2)([OH:3])=O.[CH2:22]([NH:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[CH:30]1([N:29]([CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:12]=2[CH2:13][CH2:14][C:15](=[O:21])[NH:16]3)=[O:3])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 204463Benzenemethanamine, N-cyclohexyl-HCID 12819300HCID 12819300, compound

Product 1

HCID 20563557HCID 20563557, compoundYield 23.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2.9 g of 5-(6-carboxyhexyloxy)-3,4-dihydrocarbostyril and 1.9 g of N-benzylcyclohexylamine in 100 ml of DMF is added gradually dropwise a solution of 2.1 g of N,N'-dicyclohexylcarbodiimide in 10 ml of DMF at room temperature and under agitation. After this agitation, the mixture is further agitated at room temperature for 5 hours. After the reaction, the insolubles are filtered off and the mother liquor is concentrated. The residue is dissolved in chloroform and subjected to silica gel thin-layer chromatography (solvent: chloroform-methanol (8:1) to scrape out the portion with Rf value of 0.8. The silica gel is extracted with chloroform, and after distilling off chloroform, the residue is recrystallized from benzene-ligroin to obtain 1.1 g of 5-[6-(N-cyclohexyl-N-benzylaminocarbonyl)hexyloxy]-3,4-dihydrocarbostyril in the form of colorless needle-like crystals with melting point of 49°-52° C.

Workup

  1. customAfter the reaction
  2. filtrationthe insolubles are filtered off
  3. concentrationthe mother liquor is concentrated
  4. dissolutionThe residue is dissolved in chloroform
  5. extractionThe silica gel is extracted with chloroform
  6. distillationafter distilling off chloroform
  7. customthe residue is recrystallized from benzene-ligroin

Sources & evidence

ORD record
ord-add44c1406b14d88bdea036fe2dcc5e0
Source dataset
uspto-grants-1981_11
Patent number
US04298739

Reaction notes

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