Ammonium Chloride → HCID 23121976, compound

HRID 1713488Notes

Reaction equation

HRID 1713488 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([CH2:14]C3C=CC=CC=3)[CH2:10][CH:9]2[C:21]([O:23]CC)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:26]([Mg]Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[Cl-].[NH4+]>O1CCCC1>[C:27]1([CH2:26][C:21]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([CH:9]2[CH2:10][N:11]([CH2:14][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:12][CH2:13][N:8]2[CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[OH:23])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2736402Ethyl 1,4-dibenzylpiperazine-2-carboxylateHCID 178419663HCID 178419663, compound

Product 1

HCID 23121976HCID 23121976, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl 1,4-bis(phenylmethyl)-2-piperazine carboxylate (8.2 g, 24 mmol) was dissolved in tetrahydrofuran (100 mL) under argon atmosphere. With ice cooling, a 1.0 M solution of benzyl magnesium bromide in tetrahydrofuran (100 mL, 0.10 mol) was added dropwise thereto over 30 minutes. After stirring at room temperature for 14 hours, an aqueous saturated ammonium chloride solution (300 mL) was added dropwise thereto with ice cooling, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane to hexane:ethyl acetate=5:1) to obtain the title compound (5.1 g, yield 44%).

Workup

  1. extractionwith ice cooling, and the mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (hexane to hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-016f9ba83a00491683fe7053e335b16b
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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