Toluene → HCID 67823394, compound

HRID 359405Notes

Reaction equation

HRID 359405 reaction equation
[NH2-].[Na+].CC1C=CC=CC=1.[C:10]1([CH2:16][C:17]#[N:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:19]1([CH2:25][N:26]2[CH2:31][CH2:30][CH:29]([C:32](OCC)=[O:33])[CH2:28][CH2:27]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1C=CC=CC=1.C(O)C>[OH:33][C:32]([CH:29]1[CH2:28][CH2:27][N:26]([CH2:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:31][CH2:30]1)=[C:16]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:17]#[N:18]

Participants

7

Reactant 4

HCID 1140Toluene3×HCID 8794PhenylacetonitrileHCID 24533Sodium amideHCID 90423Ethyl 1-benzylpiperidine-4-carboxylate

Product 1

HCID 67823394HCID 67823394, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Conditions

Temperature
30 °C

Procedure

To a stirred mixture of 7.8 parts of sodium amide 5% in benzene and 135 parts of methylbenzene was added dropwise a solution of 11.7 parts of benzeneacetonitrile in 45 parts of methylbenzene at 25° C. (cooling was necessary). After stirring for 30 minutes at 30° C., there was added dropwise a solution of 24.7 parts of ethyl 1-(phenylmethyl)-4-piperidinecarboxylate in 45 parts of methylbenzene at 30° C. Upon completion, stirring was continued overnight at 80° C. The reaction mixture was cooled, 12 parts of ethanol were added and the whole was poured into ice water. The layers were separated and the aqueous phase was neutralized with acetic acid. The oily product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from 4-methyl-2-pentanone, yielding 12 parts (38%) of α-[hydroxy[1-(phenylmethyl)-4-piperidinyl]methylidene]benzeneacetonitrile; mp. 191.9° C. (intermediate 5).

Workup

  1. temperature(cooling was necessary)
  2. stirringUpon completion, stirring
  3. waitwas continued overnight at 80° C
  4. temperatureThe reaction mixture was cooled
  5. customThe layers were separated
  6. extractionThe oily product was extracted with trichloromethane
  7. customThe extract was dried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was crystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-d7e31c29d6f046439b3b7205658bbe95
Source dataset
uspto-grants-1991_03
Patent number
US05001125

Reaction notes

Loading…