Sodium Hydroxide → 2,2-Diphenyl-4-(4-phenylpiperidino)butyronitrile

HRID 972549

Reaction equation

HRID 972549 reaction equation
[C:1]1([C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:10][CH2:11]Br)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:19]1([CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)C(C)C)(C)C.[OH-].[Na+]>COCCO>[C:1]1([C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:10][CH2:11][N:28]2[CH2:29][CH2:30][CH:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:26][CH2:27]2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 698734-PhenylpiperidineHCID 81531DiisopropylethylamineHCID 965754-Bromo-2,2-diphenylbutyronitrile

Product 1

HCID 214047972,2-Diphenyl-4-(4-phenylpiperidino)butyronitrile

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 18.6 parts of 2,2-diphenyl-4-bromobutyronitrile, 10.0 parts of 4-phenylpiperidine, 8.0 parts of N,N-diisopropylethylamine and 200 parts by volume of 2-methoxyethanol is heated at reflux for 16 hours. The solution is then cooled and stripped in vacuum. The resulting residue is partitioned between dilute sodium hydroxide and ether. Extraction of the ether phase with dilute hydrochloric acid results in the precipitation of an oil. This oil and the aqueous phase of the partitioning are combined, treated with aqueous sodium hydroxide and extracted with 1:1 ether-benzene mixture. The ether-benzene extract is dried over sodium sulfate and stripped in vacuum to give a solid. Crystallization of the solid from a mixture of skelly B and ether provided 2,2-diphenyl-4-(4-phenylpiperidino)butyronitrile, melting at 88° - 89.5° C. and having the following formula ##STR7##

Workup

  1. temperatureis heated
  2. temperatureat reflux for 16 hours
  3. temperatureThe solution is then cooled
  4. customThe resulting residue is partitioned between dilute sodium hydroxide and ether
  5. extractionExtraction of the ether phase with dilute hydrochloric acid
  6. customresults in the precipitation of an oil
  7. extractionextracted with 1:1 ether-benzene mixture
  8. extractionThe ether-benzene extract
  9. dry with materialis dried over sodium sulfate
  10. customto give a solid
  11. customCrystallization of the solid
  12. additionfrom a mixture of skelly B and ether

Sources & evidence

ORD record
ord-80f40e08ab6c4dbaa52aaa3b6f595c62
Source dataset
uspto-grants-1977_10
Patent number
US04053477

Linked notes

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