Cadaverine → HCID 13357000, compound

HRID 1709360Notes

Reaction equation

HRID 1709360 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].[CH2:8]([O:15][C:16](Cl)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[CH2:8]([O:15][C:16]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:16]([O:15][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:17])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 273CadaverineHCID 10387Benzyl chloroformate

Product 1

HCID 13357000HCID 13357000, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under N2, 1,5-diaminopentane (2.86 ml., 2.5 g., 0.0245 mol) was dissolved in 50 ml. CH2Cl2 and cooled to 0°. With stirring, benzyloxycarbonyl chloride (3.67 ml., 4.17 g., 0.0245 mol) was added dropwise, maintaining the temperature near 0°. The mixture was warmed to room temperature, washed 2×50 ml. 5% HCl, 1×50 ml. saturated NaHCO3, and 1×50 ml. brine, dried (MgSO4) and stripped to yield title product as a white solid, 4 g.; 1H-nmr (CDCl3) includes delta 5.2 ppm (s, 4H, two benzyl CH2 groups). The yield is greatly enhanced by use of two molar equivalents of the acid chloride.

Workup

  1. temperaturemaintaining the temperature near 0°
  2. washwashed 2×50 ml
  3. dry with materialbrine, dried (MgSO4)

Sources & evidence

ORD record
ord-09b2143f9d0248e88cc6de20f02262e5
Source dataset
uspto-grants-1990_08
Patent number
US04948913

Reaction notes

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