Potassium Carbonate → HCID 21506793, compound

HRID 1287858Notes

Reaction equation

HRID 1287858 reaction equation
[C:1]([C:3]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH2:10][CH2:11][C:12]([O:14]CC)=O)[CH2:4][C:5]([O:7]CC)=O)#[N:2].C(=O)([O-])[O-:24].[K+].[K+]>>[NH:2]1[C:12](=[O:14])[CH2:11][CH2:10][C:3]2([C:17]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:5](=[O:7])[C:4]2=[O:24])[CH2:1]1

Participants

3

Reactant 2

HCID 11430Potassium CarbonateHCID 21506791Diethyl 3-cyano-3-phenylhexanedioate

Product 1

HCID 21506793HCID 21506793, compoundYield 4.4%

Procedure

A mixture of 310 grams of polyphosphoric acid and 30.24 grams (0.1 M) of diethyl β-cyano-β-phenyladipate, prepared by the general method of Branchini et al., Annali di Chimica, 51, 1382 (1961), Chem. Abstr., 56, 15362f (1962), were heated and stirred under nitrogen atmosphere on a steam bath for five hours. The reaction mixture was poured into an icewater slurry keeping the mixture temperature at about 10° C. by additions of crushed ice. Solid potassium carbonate was added to the reaction mixture until the pH was five. On cooling overnight, a precipitate formed. Careful crystallization from acetone and then from isopropyl alcohol gave 1.1 grams (4.4%) of spiro-[indane-1,3'-piperidine]-2,3,6'-trione, melting point 227°-228° C.

Workup

  1. customprepared by the general method of Branchini et al., Annali
  2. additionThe reaction mixture was poured into an icewater slurry
  3. customat about 10° C.
  4. temperatureOn cooling overnight
  5. customa precipitate formed
  6. customCareful crystallization from acetone

Sources & evidence

ORD record
ord-2454eca759a044e8bac9441771dcb736
Source dataset
uspto-grants-1976_10
Patent number
US03985888

Reaction notes

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