Cadaverine → HCID 13357000, compound

HRID 568770Notes

Reaction equation

HRID 568770 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-f93129f14e3943ddb2acc80cc661d54f
Source dataset
uspto-grants-1988_03
Patent number
US04729985

Reaction notes

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