Dicyclohexylcarbodiimide → N-[p-(3-methylbutoxy)benzyl]-2-(3-pyridyl)thiazolidine-4-carboxamide

HRID 704435

Reaction equation

HRID 704435 reaction equation
[CH3:1][CH:2]([CH3:14])[CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH2:11])=[CH:8][CH:7]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]2[NH:25][CH:24]([C:26](O)=[O:27])[CH2:23][S:22]2)[CH:16]=1.C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C>[CH3:1][CH:2]([CH3:14])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][NH:11][C:26]([CH:24]2[CH2:23][S:22][CH:21]([C:17]3[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=3)[NH:25]2)=[O:27])=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 3275932-(3-Piridyl)thiazolidine-4-carboxylic acidHCID 8084254-(3-Methyl-butoxy)-benzylamine

Product 1

HCID 15306325N-[p-(3-methylbutoxy)benzyl]-2-(3-pyridyl)thiazolidine-4-carboxamideYield 97.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.13 g of p-(3 methylbutoxy)benzylamine, 1.29 g of 2-(3-pyridyl)thiazolidine-4-carboxylic acid, 1.25 g of dicyclohexylcarbodiimide and 0.82 g of 1-hydroxybenzotriazole in 20 ml of N,N-dimethylformamide was stirred overnight at room temperature. The reaction mixture was diluted with 100 ml of ethyl acetate, and the insoluble matter was filtered off. The filtrate was washed in sequence with saturated aqueous solution of sodium hydrogen carbonate, water and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure Purification of the thus-obtained residue by silica gel column chromatography (eluent: ethyl acetate) gave 2.20 g of N-[p-(3-methylbutoxy)benzyl]-2-(3-pyridyl)thiazolidine-4-carboxamide. To a solution of this compound in 60 ml of ethyl acetate was added 4 ml of 4N hydrogen chloride solution in dioxane. The precipitate solid was collected by filtration, washed with ethyl acetate and dried under reduced pressure to give 2.30 g of N-[p-(3-methylbutoxy)benzyl]-2-(3-pyridyl)thiazolidine-4-carboxamide dihydrochloride. Melting point 120°-128° C.

Workup

  1. filtrationthe insoluble matter was filtered off
  2. washThe filtrate was washed in sequence with saturated aqueous solution of sodium hydrogen carbonate, water and saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure Purification of the thus-obtained residue by silica gel column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-e4529035614741248b3c2d5fb4b1f7cb
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Linked notes

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