Water → HCID 21830872, compound

HRID 2393431Notes

Reaction equation

HRID 2393431 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:25][CH2:26][CH:27]1[O:31][CH2:30][CH2:29][O:28]1.O>CN(C)C=O>[CH2:3]([N:10]1[CH2:11][CH2:12][N:13]([C:16](=[O:23])[CH:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:25][CH2:26][CH:27]2[O:31][CH2:30][CH2:29][O:28]2)[CH2:14][CH2:15]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 21830850HCID 21830850, compound

Product 1

HCID 21830872HCID 21830872, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of sodium hydride (60% dispersion in oil, 1.4 g) in anhydrous dimethylformamide (50 ml) was added dropwise, under nitrogen, a solution of 4-benzyl-1-[(ethoxycarbonyl)acetyl]-piperazine (8.5 g, 29.3 mmol) in anhydrous dimethylformamide (50 ml) over 25 minutes at room temperature. After a further 30 minutes at room temperature, 2-(2-bromoethyl)-1,3-dioxolane (3.6 ml, 30.7 mmol) was added dropwise over 3 minutes and the resulting yellow solution was stirred for 24 hours. Water (400 ml) was added and products were extracted with diethyl ether (3×300 ml). The combined ethereal phases were washed with brine (1×150 ml), dried (MgSO4) and concentrated. Flash chromatography of the residue (silica gel, diethyl ether--ethanol, 95:5) afforded 8 g of the title compound (70%) as a colourless oil, δ (360 MHz, CDCl3), 1.25 (3H, t, J=7.1Hz), 1.56-1.78 (2H, m), 2.06 (2H, q, J=7.4Hz), 2.44 (4H, br s), 3.46-3.96 (11H, m), 4.16 (2H, q, J=7.1Hz), 4.86 (1H, t, J=4.6Hz), 7.24-7.36 (5H, m); m/e (ES) 391 (M+1)+.

Workup

  1. additionwas added dropwise, under nitrogen
  2. extractionproducts were extracted with diethyl ether (3×300 ml)
  3. washThe combined ethereal phases were washed with brine (1×150 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2d72334e0a1b44e8bf87fa6c799a47ea
Source dataset
uspto-grants-1998_09
Patent number
US05807857

Reaction notes

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