Ammonium Chloride → 1-(1-Benzyl-4-methyl-piperidin-4-yl)-4-methyl-piperazine

HRID 730633Notes

Reaction equation

HRID 730633 reaction equation
C[Mg]Cl.[CH2:4]([N:11]1[CH2:16][CH2:15][C:14]([N:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)([C:17]#N)[CH2:13][CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[NH4+].[Cl-]>C1COCC1>[CH2:4]([N:11]1[CH2:16][CH2:15][C:14]([N:19]2[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]2)([CH3:17])[CH2:13][CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 579896001-Benzyl-4-(4-methyl-piperazin-1-yl)-piperidin-4-carbonitrileHCID 178418332HCID 178418332, compound

Product 1

HCID 672729861-(1-Benzyl-4-methyl-piperidin-4-yl)-4-methyl-piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10 mL methylmagnesium chloride solution (30 mmol, 3 M in THF) were added at RT to a solution of 3.0 g (10.1 mmol) 1-benzyl-4-(4-methyl-piperazin-1-yl)-piperidin-4-carbonitrile in 50 mL dry THF and the reaction mixture was stirred for 2 h. It was combined with saturated NH4Cl solution, stirred for 10 min, extracted exhaustively with diethyl ether and the combined organic phases were dried on Na2SO4. After the elimination of the desiccant and solvent the residue was purified by chromatography (Alox, activity stage II-III, gradient DCM/MeOH 100:1 to 50:1).

Workup

  1. stirringstirred for 10 min
  2. extractionextracted exhaustively with diethyl ether
  3. customthe combined organic phases were dried on Na2SO4
  4. customAfter the elimination of the desiccant and solvent the residue was purified by chromatography (Alox, activity stage II-III, gradient DCM/MeOH 100:1 to 50:1)

Sources & evidence

ORD record
ord-69d99ebcf57a4ac9a07f32495699c289
Source dataset
uspto-grants-2009_09
Patent number
US07582625B2

Reaction notes

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