Triethylamine → HCID 14887125, compound

HRID 1084689Notes

Reaction equation

HRID 1084689 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][C:6]1=[O:10].C(N(CC)CC)C.Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>C(Cl)Cl>[CH2:22]([O:21][C:19]([NH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][C:6]1=[O:10])=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 821111-(3-Aminopropyl)-2-pyrrolidinone

Product 1

HCID 14887125HCID 14887125, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. solution of 1-(3-aminopropyl)-2-pyrrolidinone (25.0 g; 176 mmol) and triethylamine (26.7 g; 264 mmol) in CH2Cl2 (500 mL) was added benzyl chloroformate (33.1 g; 194 mmol) dropwise over a period of 15 minutes. The mixture was stirred for 1.5 hr. at 0° C. and then for 15 hr. at ambient temperature, before the mixture was diluted with CH2Cl2 and extracted with 5% aqueous HCl (200 mL), H2O (200 mL), and saturated aqueous NaHCO3. The organic phase was dried (MgSO4), filtered, and the solvents were removed under reduced pressure, then the oil which resulted was flash chromatographed (SiO2 ; 2-5% MeOH/Ch2Cl2) to give the title compound as a colorless oil (42.7 g; 88% yield).

Workup

  1. waitat 0° C. and then for 15 hr
  2. extractionextracted with 5% aqueous HCl (200 mL), H2O (200 mL), and saturated aqueous NaHCO3
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customthe oil which resulted
  7. customchromatographed (SiO2 ; 2-5% MeOH/Ch2Cl2)

Sources & evidence

ORD record
ord-ff3067ac8f2a449ba7f2d87a4ed63590
Source dataset
uspto-grants-1991_04
Patent number
US05006511

Reaction notes

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