Acetic Acid → HCID 53681071, compound

HRID 1384860Notes

Reaction equation

HRID 1384860 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])#[N:17].C([O-])(=O)C.[NH4+].C(O)(=O)C>C1C=CC=CC=1.C(OCC)(=O)C.O>[CH2:22]([O:21][C:19](=[O:20])[C:18](=[C:12]1[CH2:13][CH2:14][N:9]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:10][CH2:11]1)[C:16]#[N:17])[CH3:23]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 90583N-Benzoyl-4-piperidoneHCID 517165Ammonium Acetate

Product 1

HCID 53681071HCID 53681071, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-benzoyl-4-piperidone (20.0 g, 0.1 mol), ethyl cyanoacetate (10.9 ml, 0.1 mol), ammonium acetate (2.0 g) and acetic acid (6 ml) in benzene (100 ml) was heated at reflux temperature in a 3-nacked reaction flask equipped with a Dean-Stark water trap for 1 h. The cooled reaction mixture was diluted with ethyl acetate (100 ml) washed with water (3×100 ml), saturated aqueous sodium chloride (80 ml), dried (MgSO4) filtered and evaporated in vacuo affording quantitative yield of (1-benzoyl-piperidin-4-ylidene)-cyano-acetic acid ethyl ester as a slowly crystallising oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature in a 3-nacked reaction flask
  3. customThe cooled reaction mixture
  4. washwashed with water (3×100 ml), saturated aqueous sodium chloride (80 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-170795c1795b45dc97d76f58d307352c
Source dataset
uspto-grants-2001_07
Patent number
US06262044B1

Reaction notes

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