Ethyl 4-oxo-1-piperidinecarboxylate → HCID 68704856, compound

HRID 1744962Notes

Reaction equation

HRID 1744962 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].CO[CH:15](OC)[N:16]([CH3:18])[CH3:17]>O>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][C:9](=[O:12])[C:10](=[CH:15][N:16]([CH3:18])[CH3:17])[CH2:11]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 34767Ethyl 4-oxo-1-piperidinecarboxylateHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 68704856HCID 68704856, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a round bottomed flask was loaded 8.56 grams of 4-oxo-piperidine-1-carboxylic acid ethyl ester, 10.3 ml of dimethylformamide dimethylacetal, and the mixture was refluxed at 90° C. for two hours. Then it was poured into 75 ml water and extracted with 2×250 ml dichloromethane. The combined organic layers was washed with 50 ml brine and dried over magnesium sulfate. Filter off the drying agent and concentrate gave 28 grams of 3-Dimethylaminomethylene-4-oxo-piperidine-1-carboxylic acid ethyl ester. This material (12.8 grams) was then loaded into a round bottomed flask along with 3.42 grams of (5-Amino-1H-[1,2,4]triazol-3-yl)-methanol and 100 ml 2-methoxyethanol. The mixture was refluxed for 18 hours. Then it was cooled down to 23° C. and concentrated to 5 ml. Then 50 ml ethyl ether was added and the precipitate was filtered and vaccum dried to yielded 1.5 grams of product. MS: 278.1 (M+H). H-NMR(CDCL3): δ 8.60(s, 1H), 4.98(s, 2H), 4.78(s, 2H, CH2), 4.22(q, 2H, J=4.8 Hz), 3.75 (t, 2H, CH2, J=4 Hz), 3.51 (t, 2H, J=4 Hz), 1.32 (m, 3H, CH3, J=4.8 Hz).

Workup

  1. customTo a round bottomed flask was loaded
  2. extractionextracted with 2×250 ml dichloromethane
  3. washThe combined organic layers was washed with 50 ml brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationFilter off the drying agent
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-1a420ef8cd054f569b30ae8c2a5bd96f
Source dataset
uspto-grants-2006_03
Patent number
US07018997B2

Reaction notes

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