4-Methylmorpholine → HCID 53679744, compound

HRID 704440Notes

Reaction equation

HRID 704440 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][NH:10][CH2:11][CH2:12][NH2:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN1CCOCC1.ON1C2C=CC=CC=2N=N1.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH:37]2[NH:41][CH:40]([C:42](O)=[O:43])[CH2:39][S:38]2)[CH:32]=1>CN(C)C=O.C(OCC)(=O)C>[C:1]1([CH2:7][CH2:8][CH2:9][NH:10][CH2:11][CH2:12][NH:13][C:42]([CH:40]2[CH2:39][S:38][CH:37]([C:33]3[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=3)[NH:41]2)=[O:43])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 3275932-(3-Piridyl)thiazolidine-4-carboxylic acidHCID 11105931N1-(3-Phenylpropyl)-1,2-ethanediamine

Product 1

HCID 53679744HCID 53679744, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 200 mg of 3-phenylpropylethylenediamine and 81 mg of N-methylmorpholine in 5 ml of dimethylformamide, there were added in sequence 120 mg of 1-hydroxybenzotriazole, 180 mg of dicyclohexylcarbondiimide and 170 mg of 2-(3-pyridyl)thiazolidine-4-carboxylic acid. The mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, the insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. After addition of 0.5N aqueous sodium hydroxide, the residue was extracted with ethyl acetate. The organic layer was extracted with 1N hydrochloric acid, and the aqueous layer was adjusted to pH 10 with potassium carbonate and extracted again with ethyl acetate The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to alumina column chromatography (20 g). Elution with methanol-ethyl acetate (1:10) gave 160 mg of N-(3-phenylpropylaminoethyl)-2-(3-pyridyl)thiazolidine-4-carboxamide. The NMR and MS data for this compound were in agreement with those given in Examples 115.

Workup

  1. filtrationthe insoluble matter was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionAfter addition of 0.5N aqueous sodium hydroxide
  4. extractionthe residue was extracted with ethyl acetate
  5. extractionThe organic layer was extracted with 1N hydrochloric acid
  6. extractionextracted again with ethyl acetate The organic layer
  7. washwas washed with saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. washElution with methanol-ethyl acetate (1:10)

Sources & evidence

ORD record
ord-087fd8d22c724c6fb8f8676173ca3d22
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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