Putrescine → HCID 14548422, compound

HRID 565611Notes

Reaction equation

HRID 565611 reaction equation
[CH2:1]([NH2:6])[CH2:2][CH2:3][CH2:4][NH2:5].[C:7]1(=[O:14])[O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[OH-:15].[Na+]>C1COCC1.O.CO>[CH2:1]([NH:6][C:12](=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][OH:15])[CH2:2][CH2:3][CH2:4][NH:5][C:7](=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13]

Participants

7

Reactant 3

HCID 1045PutrescineHCID 10401epsilon-CAPROLACTONEHCID 14798Sodium Hydroxide

Product 1

HCID 14548422HCID 14548422, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 8.35 gram (0.0949 mol) 1,4-butanediamine in a mixture of 25 ml THF and 5 ml H2O was added a solution of 21.66 gram (0.1897 mol) ε-caprolactone in 25 ml THF in 5 min. at room temperature while stirring. The reaction mixture was stirred for 16 hours, whereafter the solvent was evaporated under reduced pressure. The obtained crude product (light yellow oil) was dissolved in 150 ml methanol (p.a.) and brought to pH=11.5 by adding 1M NaOH. The obtained solution was stirred for 16 hours whereafter it was added slowly drop by drop to 500 ml THF (p.a.). The obtained white product was filtered off and dried. The product still contains crystallization water. Yield 70%; Tm=135-136° C. C16H32N2O4: C, H, N; calculated 60.71%, 10.20%, 8.86%; found 58.87%, 10.13%, 8.44%.

Workup

  1. stirringThe reaction mixture was stirred for 16 hours, whereafter the solvent
  2. customwas evaporated under reduced pressure
  3. customThe obtained crude product (light yellow oil)
  4. stirringThe obtained solution was stirred for 16 hours whereafter it
  5. filtrationThe obtained white product was filtered off
  6. customdried
  7. customThe product still contains crystallization water
  8. customTm=135-136° C

Sources & evidence

ORD record
ord-77bab51031ca4696ad2aed96edac979b
Source dataset
uspto-grants-2001_01
Patent number
US06172167B2

Reaction notes

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