Cadaverine → N-Carbobenzoxy-1,5-diaminopentane hydrochloride

HRID 973737Notes

Reaction equation

HRID 973737 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14]SC1=S)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17][CH2:18][CH2:19][CH2:20]CCN>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][CH2:15][CH2:14][CH2:20][CH2:19][CH2:18][NH2:17])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 273CadaverineHCID 12706814Benzyl 2-sulfanylidene-1,3-thiazolidine-3-carboxylate

Product 1

HCID 2794259N-Carbobenzoxy-1,5-diaminopentane hydrochlorideYield 63.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

17.84 g of the product of Step A in solution in 100 ml of methylene chloride were added to 16.4 g of 1,5-diamino-pentane in solution in 85 ml of methylene chloride and after stirring for 3 hours and concentration to dryness, the residue was chromatographed (eluant: methanol-ammonia 99-1) to obtain 10.5 g of the expected product.

Workup

  1. concentrationconcentration to dryness
  2. customthe residue was chromatographed (eluant: methanol-ammonia 99-1)

Sources & evidence

ORD record
ord-eeb5828e9add42bbb6bdf42e43004506
Source dataset
uspto-grants-1991_11
Patent number
US05064861

Reaction notes

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