Water → HCID 19778051, compound

HRID 2082315Notes

Reaction equation

HRID 2082315 reaction equation
Cl.Cl.[N:3]1([C:8]2[CH:22]=[CH:21][C:11]([C:12]([N:14]3[CH2:19][CH2:18][CH:17]([NH2:20])[CH2:16][CH2:15]3)=[O:13])=[CH:10][CH:9]=2)[CH:7]=[CH:6][N:5]=[CH:4]1.C(=O)([O-])[O-].[K+].[K+].O.[C:30]1([CH2:36][CH2:37][C:38](Cl)=[O:39])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl>[N:3]1([C:8]2[CH:9]=[CH:10][C:11]([C:12]([N:14]3[CH2:19][CH2:18][CH:17]([NH:20][C:38](=[O:39])[CH2:37][CH2:36][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH2:16][CH2:15]3)=[O:13])=[CH:21][CH:22]=2)[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 64801Benzenepropanoyl chlorideHCID 19778043HCID 19778043, compound

Product 1

HCID 19778051HCID 19778051, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-[4-(1H-Imidazol-1-yl)benzoyl]-4-piperidinamine dihydrochloride (4.46 g, 13.0 mmol) and potassium carbonate (6.67 g, 52.0 mmol) are dissolved in methylene chloride (60 mL) and water (30 mL) and the mixture is cooled with an ice bath. A solution of 3-phenylpropionyl chloride (2.72 g, 16.2 mmol) in methylene chloride (15 mL) is added dropwise over 15 min, and the mixture is stirred at room temperature for 2 hr. The phases are separated, and the organic phase is washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, and evaporated. Chromatography of the residue on silica gel followed by recrystallization from acetonitrile affords the title compound.

Workup

  1. customThe phases are separated
  2. washthe organic phase is washed with saturated aqueous sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customChromatography of the residue on silica gel followed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-0490c631d8854caabbdb9581bebba071
Source dataset
uspto-grants-1993_02
Patent number
US05189036

Reaction notes

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