Ammonium Chloride → HCID 23441029, compound

HRID 2119351Notes

Reaction equation

HRID 2119351 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[CH2:13][CH2:12][CH2:11][N:10]([CH2:14][CH2:15][C:16]([O:18]C)=O)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[C:22]1([Mg]Br)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-].[NH4+]>CCOCC>[OH:18][C:16]([C:2]1[CH:21]=[CH:20][CH:5]=[CH:4][CH:3]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:15][CH2:14][N:10]1[CH2:11][CH2:12][CH2:13][N:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:21][CH:20]=2)[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23441062HCID 23441062, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 23441029HCID 23441029, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 54 mg of methyl 3-[4-(4-chlorobenzyl) homopiperazinyl]propionate in 10 mL of ether was mixed with under nitrogen, 4 mL of 1 M phenyl magnesium bromide. The mixture was stirred at room temperature for 30 minutes, mixed with aqueous saturated ammonium chloride and the mixture was extracted with 50 mL of ethyl acetate. The extract was washed with 50 mL of saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by column chromatography (silica gel, ethyl acetate/methanol 9:1) to give 65 mg of the titled compound. This was treated with a hydrogen chloride solution in ether and the solvent was removed under reduced pressure and the residue was dried to give the hydrochloride salt of the titled compound.

Workup

  1. extractionthe mixture was extracted with 50 mL of ethyl acetate
  2. washThe extract was washed with 50 mL of saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography (silica gel, ethyl acetate/methanol 9:1)

Sources & evidence

ORD record
ord-8227d598a9e74725a8a0028d9e25d6da
Source dataset
uspto-grants-2004_02
Patent number
US06686353B1

Reaction notes

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