Putrescine → Benzyl N-(4-aminobutyl)carbamate

HRID 463449Notes

Reaction equation

HRID 463449 reaction equation
[CH2:1]([NH2:6])[CH2:2][CH2:3][CH2:4][NH2:5].[CH2:7]([O:14][C:15](SC1N=C(C)C=C(C)N=1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CO>[CH2:7]([O:14][C:15]([NH:5][CH2:4][CH2:3][CH2:2][CH2:1][NH2:6])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 1045PutrescineHCID 563496Benzyl S-4,6-dimethylpyrimidin-2-yl thiocarbonate

Product 1

HCID 2783677Benzyl N-(4-aminobutyl)carbamateYield 23%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into 30 mL of 50% aqueous methanol, was dissolved 1.76 g (20 mmoles) of 1,4-butanediamine followed by the addition of 5.48 g (20 mmoles) of S-benzyloxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine (a product of Kokusan Kagaku Co.). The mixture was stirred for 3 hours. Thereafter, the reaction mixture was filtered to remove the precipitated di-N-benzyloxycarbonyl compound [2.09 g (29%) were recovered], and the filtrate was evaporated to dryness. The residue was dissolved in 250 mL of chloroform, washed 5 times with 100 mL of water. The chloroform layer was dried over anhydrous sodium sulfate, and evaporated to dryness to obtain 1.0 g (23% yield) of mono-N-benzyloxycarbonyl-1,4-butanediamine in colorless syrup form.

Workup

  1. filtrationThereafter, the reaction mixture was filtered
  2. customto remove the precipitated di-N-benzyloxycarbonyl compound [2.09 g (29%) were recovered]
  3. customthe filtrate was evaporated to dryness
  4. dissolutionThe residue was dissolved in 250 mL of chloroform
  5. washwashed 5 times with 100 mL of water
  6. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-3ada78469249495ea31384774e4b3f03
Source dataset
uspto-grants-1985_05
Patent number
US04518802

Reaction notes

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