Sodium Hydroxide → 1-Amidino-4-piperidinepropionic acid

HRID 1388840Notes

Reaction equation

HRID 1388840 reaction equation
[OH-].[Na+].CO[C:5]([NH2:7])=[NH:6].OS(O)(=O)=O.[NH:13]1[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH2:15][CH2:14]1>O>[C:5]([N:13]1[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH2:15][CH2:14]1)(=[NH:6])[NH2:7]

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 169039Carbamimidic acid, methyl ester, sulfate (1:1)HCID 15208063-(Piperidin-4-yl)propanoic acid

Product 1

HCID 155835111-Amidino-4-piperidinepropionic acidYield 50.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20 ml of 2 N sodium hydroxide was stirred with ice-cooling, and 3.4 g of o-methylisourea sulfate and 3.1 g of piperidine-4-propionic acid were added to the aqueous sodium hydroxide solution. To the mixture was then added 5 ml of water, and the resulting mixture was stirred at room temperature for 19 hours. The product precipitated was separated by filtration and washed with a small amount of cold water three times, then with acetone and finally with ether to obtain 2.0 g of 1-amidino-4-piperidinepropionic acid as colorless crystals having a melting point of 294° C. (decomposed).

Workup

  1. temperaturecooling
  2. customThe product precipitated
  3. customwas separated by filtration
  4. washwashed with a small amount of cold water three times

Sources & evidence

ORD record
ord-4ef0174f63e94b3ca0ffad501c554f1d
Source dataset
uspto-grants-1984_02
Patent number
US04433152

Reaction notes

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