N,N'-Dimethylethylenediamine → 1-[3-(Hydroxymethyl)phenyl]-2-pyrrolidinone

HRID 1883430Notes

Reaction equation

HRID 1883430 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].CNCCNC.I[C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19][OH:20].[NH:24]1[CH2:28][CH2:27][CH2:26][C:25]1=[O:29]>[Cu]I.C1(C)C=CC=CC=1>[OH:20][CH2:19][C:18]1[CH:17]=[C:16]([N:24]2[CH2:28][CH2:27][CH2:26][C:25]2=[O:29])[CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 120252-PyrrolidoneHCID 423003-Iodobenzyl alcoholHCID 62657Potassium Phosphate, Tribasic

Product 1

HCID 219406941-[3-(Hydroxymethyl)phenyl]-2-pyrrolidinoneYield 93.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A Schlenk tube was charged with CuI (9.6 mg, 0.050 mmol, 5.0 mol %) and K3PO4 (430 mg, 2.03 mmol), evacuated and backfilled with argon. N,N′-Dimethylethylenediamine (11 μL, 0.10 mmol, 10 mol %), 3-iodobenzyl alcohol (128 μL, 1.01 mmol), 2-pyrrolidinone (94 μL, 1.24 mmol) and toluene (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 80° C. for 3 h. The resulting white suspension was allowed to reach room temperature and filtered through a 0.5×1 cm pad of silica gel eluting with 5:1 ether-methanol (10 mL). The filtrate was concentrated and the residue was purified by flash chromatography on silica gel (2×20 cm; dichloromethane-methanol 25:1; 15 mL fractions). Fractions 14-19 provided 180 mg (93% yield) of the product as a white solid. Mp: 120-121° C.

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed with a Teflon valve
  3. customto reach room temperature
  4. filtrationfiltered through a 0.5×1 cm pad of silica gel eluting with 5:1 ether-methanol (10 mL)
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by flash chromatography on silica gel (2×20 cm; dichloromethane-methanol 25:1; 15 mL fractions)

Sources & evidence

ORD record
ord-a197209cee734c2f8e32ccd0b9318926
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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