Putrescine → Benzyl N-(4-aminobutyl)carbamate

HRID 973724Notes

Reaction equation

HRID 973724 reaction equation
CS(O)(=O)=O.[NH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH2:11].Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].C([O-])(=O)C.[K+]>O.C(O)C.COCCOC>[CH2:16]([O:15][C:13]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][NH2:11])=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 1045PutrescineHCID 6395Methanesulfonic AcidHCID 10387Benzyl chloroformateHCID 517044Potassium Acetate

Product 1

HCID 2783677Benzyl N-(4-aminobutyl)carbamateYield 37.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 46 g of methane sulfonic acid in 50 ml of water was added without exceeding 30° C. to a mixture of 23 g of 1,4-diamino butane and 50 ml of water and the reaction medium was diluted with 140 ml of ethanol. A solution of 39 g of benzyl chloroformate in 50 ml of 1,2-dimethoxy ethane and 100 ml of a 50% aqueous solution of potassium acetate were added alternately at pH 3.5 to 5.0. The additions were made alternately to maintain the pH value between 3.5 and 5.0. The mixture was stirred for 90 minutes at 20° to 25° C. and evaporated under reduced pressure. The residue was poured over 500 ml of water and the insoluble part was filtered off. The filtrate was washed 3 times with 150 ml of benzene, and then 100 ml of 30% sodium hydroxide saturated with sodium chloride were added. After extraction with benzene, the extracts were evaporated to dryness under reduced pressure to obtain 19.10 g of the expected product.

Workup

  1. temperatureto maintain the pH value between 3.5 and 5.0
  2. customevaporated under reduced pressure
  3. additionThe residue was poured over 500 ml of water
  4. filtrationthe insoluble part was filtered off
  5. washThe filtrate was washed 3 times with 150 ml of benzene
  6. addition100 ml of 30% sodium hydroxide saturated with sodium chloride were added
  7. extractionAfter extraction with benzene
  8. customthe extracts were evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-21d71e76cd624a2f9595ed4e81f05101
Source dataset
uspto-grants-1991_11
Patent number
US05064861

Reaction notes

Loading…