Dimethylformamide dimethyl acetal → HCID 54308355, compound

HRID 1291825Notes

Reaction equation

HRID 1291825 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH2:8][CH2:7]1)=[O:5])[CH3:2].CO[CH:19](OC)[N:20]([CH3:22])[CH3:21]>CN(C=O)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:19][N:20]([CH3:22])[CH3:21])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetal2×HCID 18918264HCID 18918264, compound

Product 1

HCID 54308355HCID 54308355, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product of step (i) (10 g) in dry DMF (80 ml) was added dimethylformamide dimethyl acetal (DMFDMA) (30 ml) and the reaction mixture was heated to reflux. After 2 days a further quantity of DMFDMA (30 ml) was added and refluxing was continued for a further 2 days. The reaction mixture was evaporated and the residue partitioned between aqueous ammonium chloride solution and ethyl acetate. The organic layer was separated, washed with brine, dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica by elution with ethyl acetate to yield 1-ethoxycarbonyl-4-(1-dimethylamino-2-methoxycarbonylethen-2-yl)-piperazine (7 g) as an orange oil: NMR (CDCl3) δ 1.28 (3H, t), 2.90 (4H, m), 3.14 (6H, s), 3.50 (4H, m), 3.64 (3H, s), 4.12 (2H, q), 7.01 (1H, s); m/Z 286 (M+H)+.

Workup

  1. temperaturethe reaction mixture was heated to reflux
  2. temperaturerefluxing
  3. customThe reaction mixture was evaporated
  4. customthe residue partitioned between aqueous ammonium chloride solution and ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue was purified by flash chromatography on silica by elution with ethyl acetate

Sources & evidence

ORD record
ord-7fefd102ecaa4997a20239909e30170a
Source dataset
uspto-grants-1998_05
Patent number
US05753659

Reaction notes

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