Putrescine → Benzyl N-(4-aminobutyl)carbamate

HRID 978428Notes

Reaction equation

HRID 978428 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6].Cl[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9]>C(Cl)Cl>[CH2:11]([O:10][C:8]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH2:6])=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 1045PutrescineHCID 10387Benzyl chloroformate

Product 1

HCID 2783677Benzyl N-(4-aminobutyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 147 g of 1,4-diaminobutane in 490 ml of methylene chloride, a solution of 41 ml of benzyl chloroformate in 84 ml of methylene chloride was added dropwise at 0° over a period of 1 hour. The mixture was stirred at 0° for 1 hour, then washed twice with water and extracted four times with 150 ml of 4N hydrochloric acid. The acidic extracts were washed with methylene chloride, basified with 450 ml of 22% of sodium hydroxide and extracted four times with methylene chloride. The organic extracts were dried over magnesium sulfate and evaporated to give 4-benzyloxycarbonylamino-1-butylamine, having NMR peaks at δ=7.3, 5.05 and 2.6 ppm.

Workup

  1. washwashed twice with water
  2. extractionextracted four times with 150 ml of 4N hydrochloric acid
  3. washThe acidic extracts were washed with methylene chloride
  4. extractionextracted four times with methylene chloride
  5. dry with materialThe organic extracts were dried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-caa613fa438241b0b38016edaf104204
Source dataset
uspto-grants-1987_05
Patent number
US04665087

Reaction notes

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