Ammonium Chloride → HCID 66941861, compound

HRID 2106506Notes

Reaction equation

HRID 2106506 reaction equation
C[Mg]Cl.[CH2:4]([N:11]1[CH2:16][CH2:15][C:14]([N:19]2[CH2:24][CH2:23][NH:22][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][NH:22][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 20117869HCID 20117869, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 66941861HCID 66941861, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

15 mL methylmagnesium chloride solution (45 mmol, 3 M in THF) were added at RT to 2.37 g (7.92 mmol) 1-benzyl-4-piperazin-1-yl-piperidine-4-carbonitrile in 100 mL dry THF and the reaction mixture was stirred for 3 h. Saturated NH4Cl solution was added, the mixture was stirred for another 10 min, the aqueous phase was washed with EtOAc, combined with 4 M NaOH solution until an alkaline reaction was obtained, extracted exhaustively with DCM and the combined organic phases were dried over Na2SO4. After elimination of the desiccant and solvent the residue was further reacted without any further purification.

Workup

  1. stirringthe mixture was stirred for another 10 min
  2. washthe aqueous phase was washed with EtOAc
  3. customcombined with 4 M NaOH solution until an alkaline reaction
  4. customwas obtained
  5. extractionextracted exhaustively with DCM
  6. dry with materialthe combined organic phases were dried over Na2SO4
  7. customAfter elimination of the desiccant and solvent the residue was further reacted without any further purification

Sources & evidence

ORD record
ord-591aa973843e46738615a480ac1b1a41
Source dataset
uspto-grants-2009_08
Patent number
US07579341B2

Reaction notes

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