Dimethylformamide → HCID 21708626, compound

HRID 649794Notes

Reaction equation

HRID 649794 reaction equation
CN([CH:4]=[O:5])C.O=P(Cl)(Cl)Cl.[ClH:11].[N:12]12[CH2:20][CH:16]([CH2:17][CH2:18][CH2:19]1)[C:15](=O)[CH2:14][CH2:13]2.C(=O)([O-])[O-].[K+].[K+]>>[Cl:11][CH:15]1[CH:16]2[CH2:20][N:12]([CH2:19][CH2:18][CH2:17]2)[CH:13]=[C:14]1[CH:4]=[O:5]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 22504480HCID 22504480, compound

Product 1

HCID 21708626HCID 21708626, compoundYield 91.6%

Conditions

Temperature
100 °C

Procedure

To DMF (50 ml, 0.68 mol) was slowly added POCl3 (50 ml, 0.54 mol) at 0° C. over 1 h. 1-Azabicyclo[3.3.1]nonane-4-one hydrochloride (17.5 g, 0.1 mol) was added in one portion and the reaction mixture heated at 100° C. for 1 h. After cooling the reaction mixture was poured on ice (1000 g) and the reaction mixture neutralized with potassium carbonate. The water phase was extracted with ether (5×200 ml). The organic phase was dried over MgSO4 and evaporated. The residue was purified by column chromatography (eluent: CH2Cl2/CH3OH (9:1)), yielding 17 g of the title compound.

Workup

  1. customat 0° C.
  2. customover 1 h
  3. temperatureAfter cooling the reaction mixture
  4. additionwas poured on ice (1000 g)
  5. extractionThe water phase was extracted with ether (5×200 ml)
  6. dry with materialThe organic phase was dried over MgSO4
  7. customevaporated
  8. customThe residue was purified by column chromatography (eluent: CH2Cl2/CH3OH (9:1))

Sources & evidence

ORD record
ord-56bbcc4c42734674a22bc9096d4ce762
Source dataset
uspto-grants-2001_08
Patent number
US06271229B1

Reaction notes

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