Water → (2-Oxo-4-propylpyrrolidin-1-yl)methyl diethylcarbamate

HRID 1924211Notes

Reaction equation

HRID 1924211 reaction equation
[OH:1][CH2:2][N:3]1[CH2:7][CH:6]([CH2:8][CH2:9][CH3:10])[CH2:5][C:4]1=[O:11].C(N(CC)CC)C.[CH2:19]([N:21]([CH2:25][CH3:26])[C:22](Cl)=[O:23])[CH3:20].O>C(Cl)Cl>[CH2:19]([N:21]([CH2:25][CH3:26])[C:22](=[O:23])[O:1][CH2:2][N:3]1[CH2:7][CH:6]([CH2:8][CH2:9][CH3:10])[CH2:5][C:4]1=[O:11])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6916Diethylcarbamoyl chlorideHCID 8471TriethylamineHCID 113326021-(Hydroxymethyl)-4-propylpyrrolidin-2-one

Product 1

HCID 11448237(2-Oxo-4-propylpyrrolidin-1-yl)methyl diethylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 1-(hydroxymethyl)-4-propylpyrrolidin-2-one x2 (4 g, 25.44 mmol) and triethylamine (1.2 eq, 30.53 mmol, 3.089 g, 4.26 ml) in CH2Cl2 (25 ml) is added dropwise a solution of diethylcarbamyl chloride (1.1 eq, 27.99 mmol, 3.795 g, 3.55 ml) in CH2Cl2 (5 ml) at room temperature. The reaction mixture is allowed to react under agitation and inert atmosphere overnight. Hydrolysis (15 ml of water), extraction (CH2Cl2), drying of the combinated organic layers (MgSO4), filtration and solvent evaporation under reduced pressure gives (2-oxo-4-propylpyrrolidin-1-yl)methyl diethylcarbamate x6 (100%) which is used without any further purification.

Workup

  1. customto react under agitation and inert atmosphere overnight
  2. dry with materialdrying of the combinated organic layers (MgSO4), filtration and solvent evaporation under reduced pressure

Sources & evidence

ORD record
ord-bd5c6b7ab8124f49ac230ea290da003e
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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