Dimethylformamide → HCID 70508041, compound

HRID 1388855Notes

Reaction equation

HRID 1388855 reaction equation
[ClH:1].[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH2:7][CH2:6]1)(=[NH:4])[NH2:3].[C:16]([C:20]1[CH:25]=[CH:24][C:23]([SH:26])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17].C1(N=C=NC2CCCCC2)CCCCC1.CN(C)C=O>O>[ClH:1].[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][C:13]([O:15][S:26][C:23]2[CH:24]=[CH:25][C:20]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:21][CH:22]=2)=[O:14])[CH2:7][CH2:6]1)(=[NH:3])[NH2:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 754544-Tert-ButylbenzenethiolHCID 155835121-Amidino-4-piperidinepropionic acid hydrochloride

Product 1

HCID 70508041HCID 70508041, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3 g of 1-amidino-4-piperidinepropionic acid hydrochloride, 2.2 g of p-t-butyl thiophenol, 2.6 g of dicyclohexylcarbodiimide and 18 ml of dry dimethylformamide was stirred at room temperature for 10 hours. After removal of any insoluble materials, the solvent was removed under reduced pressure. The residue was washed with ether and dissolved in t-butanol. Ether was added to the solution to give an oily substance. Water was added to the oily substance, and the mixture was allowed to stand overnight in cold conditions to give crystals. The crystals were washed with ethyl acetate and then with ether and air-dried to obtain 2.3 g (yield: 46.9%) of p-t-butylphenylthio 1-amidino-4-piperidinepropionate hydrochloride as colorless crystals having a melting point of 86° to 88° C.

Workup

  1. customAfter removal of any insoluble materials
  2. customthe solvent was removed under reduced pressure
  3. washThe residue was washed with ether
  4. dissolutiondissolved in t-butanol
  5. additionEther was added to the solution
  6. customto give an oily substance
  7. waitto stand overnight in cold conditions
  8. customto give crystals
  9. washThe crystals were washed with ethyl acetate
  10. dry with materialwith ether and air-dried

Sources & evidence

ORD record
ord-4754edd4d07641a182ea6d5281e734be
Source dataset
uspto-grants-1984_02
Patent number
US04433152

Reaction notes

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