Dimethylformamide dimethyl acetal → HCID 57137764, compound

HRID 1272381Notes

Reaction equation

HRID 1272381 reaction equation
[C:1]([N:20]1[CH2:25][CH2:24][CH2:23][C:22](=[O:26])[CH2:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[CH:29]([N:32]([CH3:34])[CH3:33])OC>CN(C=O)C>[CH3:29][N:32]([CH:34]=[C:23]1[CH2:24][CH2:25][N:20]([C:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:21][C:22]1=[O:26])[CH3:33]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 227070511-Tritylpiperidin-3-one

Product 1

HCID 57137764HCID 57137764, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1.94 g (5.68 mmol) of piperidinone from Step B in 10 mL of DMF was treated with 0.677 g (0.755 mL) of 1,1-dimethoxy-N,N-dimethylmethylamine. The colorless suspension was warmed to 80° C. under nitrogen. After 18 h, the mixture was cooled to ambient temperature and concentrated in vacuo. The dark red residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate and concentrated to give 2.25 g of a pale yellow-orange foam. Crystallization of a 2.03-g portion from ether (2 crops) gave a total of 1.17 g (52%) of the title compound.

Workup

  1. temperaturethe mixture was cooled to ambient temperature
  2. concentrationconcentrated in vacuo
  3. customThe dark red residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-69123009796e4a4a96dd001566c71f8b
Source dataset
uspto-grants-2007_04
Patent number
US07208498B2

Reaction notes

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