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

HRID 1896348Notes

Reaction equation

HRID 1896348 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-2f1d7bf5791c48c1a29470924242963d
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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