Ammonium Acetate → HCID 67594506, compound

HRID 362892Notes

Reaction equation

HRID 362892 reaction equation
C([BH3-])#[N:2].[Na+].O=[C:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][S:14][C:15]2[NH:16][C:17]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:19]=2)[CH2:8][CH2:7]1.C([O-])(=O)C.[NH4+]>CO>[NH2:2][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][S:14][C:15]2[NH:16][C:17]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:19]=2)[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 67596517HCID 67596517, compound

Product 1

HCID 67594506HCID 67594506, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Step 4): Sodium cyanoborohydride (0.06 g, 9.5 mmol) was added to solution of 2-[2-(4-oxopiperidin-1-yl)ethyl]thio-4,5-diphenylimidazole (0.34 g, 0.91 mmol), powdered 3A molecular sieves (0.268 g) and ammonium acetate (0.73 g, 9.5 mmol) in methanol (10 ml). The mixture was stirred at room temperature under nitrogen atmosphere for 65 hours and then filtered and washed with methanol. The filtrate was concentrated. The residue was dissolved in 10% NaOH solution and ethyl acetate. The organic layer was washed with water and saturated NaCl solution, dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica gel (0.8% NH4OH in chloroform/methanol) to give 2-[2-(4-aminopiperidin-1-yl)ethyl]thio-4,5-diphenylimidazole (172 mg, 49.9%) as a pale yellow oil.

Workup

  1. filtrationfiltered
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated
  4. dissolutionThe residue was dissolved in 10% NaOH solution
  5. washThe organic layer was washed with water and saturated NaCl solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (0.8% NH4OH in chloroform/methanol)

Sources & evidence

ORD record
ord-763ddb93ac924736abcffd85e84b3bd2
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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