Ammonium Chloride → tert-Butyl (2R,5S)-4-(3-tert-butoxy-4-cyanophenyl)-2,5-dimethylpiperazine-1-carboxylate

HRID 1593378Notes

Reaction equation

HRID 1593378 reaction equation
F[C:2]1[CH:3]=[C:4]([N:10]2[C@@H:15]([CH3:16])[CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:12]([CH3:24])[CH2:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[CH3:25][C:26]([CH3:29])([O-:28])[CH3:27].[K+].[Cl-].[NH4+]>C1COCC1>[C:26]([O:28][C:2]1[CH:3]=[C:4]([N:10]2[C@@H:15]([CH3:16])[CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:12]([CH3:24])[CH2:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9])([CH3:29])([CH3:27])[CH3:25]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 86601755HCID 86601755, compound

Product 1

HCID 86601756tert-Butyl (2R,5S)-4-(3-tert-butoxy-4-cyanophenyl)-2,5-dimethylpiperazine-1-carboxylateYield 30.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into 20 ml of THF was dissolved 3.12 g of tert-butyl (2R,5S)-4-(3-fluoro-4-cyanophenyl)-2,5-dimethylpiperazine-1-carboxylate, and then 1.40 g of potassium tert-butoxide was added thereto, followed by heating under refluxing overnight. A saturated ammonium chloride aqueous solution was added to the reaction solution, followed by extraction with chloroform. After the organic layer was dried over anhydrous sodium sulfate, the solvent was removed by evaporation to obtain 1.11 g of the title compound.

Workup

  1. temperatureby heating
  2. temperatureunder refluxing overnight
  3. extractionfollowed by extraction with chloroform
  4. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-6a079afd12d94a3baed2f1da6f7efc67
Source dataset
uspto-grants-2007_11
Patent number
US07297698B2

Reaction notes

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