Potassium Carbonate → HCID 20374289, compound

HRID 1834146Notes

Reaction equation

HRID 1834146 reaction equation
[C:1]1([C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.Cl.[C:29]1([C:35]2([C:41]#[N:42])[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>O.C(Cl)Cl.C1C=CC=CC=1>[C:29]1([C:35]2([C:41]#[N:42])[CH2:36][CH2:37][N:38]([C:9](=[O:11])[CH2:8][C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:39][CH2:40]2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 1366963,3,3-Triphenylpropionic AcidHCID 30849734-Phenylpiperidine-4-carbonitrile hydrochloride

Product 1

HCID 20374289HCID 20374289, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent2×HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

3 Parts of 3,3,3-triphenylpropionic acid are refluxed with 1 part by volume of thionyl chloride in 25 parts by volume of benzene for about 2 hours. The reaction mixture is then cooled and poured into a mixture of 2.2 parts of 4-phenylisonipecotonitrile hydrochloride, 4.1 parts of potassium carbonate in 20 parts by volume of water and 20 parts by volume of benzene. This reacton mixture is stirred under nitrogen while cooling in an ice bath, and then methylene chloride and water are added to the reaction mixture and the 2-phase system is filtered from the solid which forms. The organic layer is separated, washed with water and with saturated sodium sulfate and dried. The solvent is evaporated to leave an oily residue which is crystallized from ether to afford 4-phenyl-1-(3,3,3-triphenyl-propionyl)isonipecotonitrile melting at about 188.5°-190.5° C. This crystalline product is identical to the aforementioned solid and is represented by the following structural formula ##STR11##

Workup

  1. temperatureThe reaction mixture is then cooled
  2. temperaturewhile cooling in an ice bath
  3. filtrationthe 2-phase system is filtered from the solid which forms
  4. customThe organic layer is separated
  5. washwashed with water and with saturated sodium sulfate
  6. customdried
  7. customThe solvent is evaporated
  8. customto leave an oily residue which
  9. customis crystallized from ether

Sources & evidence

ORD record
ord-d12a284a61744cab8461c56945e4bc28
Source dataset
uspto-grants-1978_01
Patent number
US04069223

Reaction notes

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