Ammonium Chloride → 2-(3-(4-(4-Methoxybenzoyl)piperidin-1-yl)-2-oxopyrrolidin-1-yl)acetimidamide hydrochloride

HRID 1752248Notes

Reaction equation

HRID 1752248 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([CH:15]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]#[N:22])[C:16]3=[O:23])[CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.[Cl-:26].[NH4+:27]>CO.C[O-].[Na+]>[ClH:26].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([CH:9]2[CH2:10][CH2:11][N:12]([CH:15]3[CH2:19][CH2:18][N:17]([CH2:20][C:21](=[NH:27])[NH2:22])[C:16]3=[O:23])[CH2:13][CH2:14]2)=[O:8])=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 893757962-(3-(4-(4-Methoxybenzoyl)piperidin-1-yl)-2-oxopyrrolidin-1-yl)acetonitrile

Product 1

HCID 893757462-(3-(4-(4-Methoxybenzoyl)piperidin-1-yl)-2-oxopyrrolidin-1-yl)acetimidamide hydrochlorideYield 101.3%

Reagents, catalysts & solvents 2

HCID 10942334Sodium MethoxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(3-(4-(4-methoxybenzoyl)piperidin-1-yl)-2-oxopyrrolidin-1-yl)acetonitrile (690 mg, 2.0 mmol) in methanol (15 mL) was added sodium methoxide (0.046 mL, 0.20 mmol, 25%) and the mixture was stirred at ambient temperature for 2 h. Ammonium chloride (120 mg, 2.3 mmol) was added and the mixture was stirred at ambient temperature for 60 h. The reaction mixture was concentrated in vacuo, ethyl acetate in heptane (40%) was added, stirred at ambient temperature for 1 h then filtrated. the resulting solid was washed with ether to give a pale solid (800 mg, 100% yield). MS m/z 342.4 (M+1), retention time 0.79

Workup

  1. stirringthe mixture was stirred at ambient temperature for 60 h
  2. concentrationThe reaction mixture was concentrated in vacuo, ethyl acetate in heptane (40%)
  3. additionwas added
  4. stirringstirred at ambient temperature for 1 h
  5. filtrationthen filtrated
  6. washthe resulting solid was washed with ether

Sources & evidence

ORD record
ord-7a774b49d8e74e64984cf04a03c9c462
Source dataset
uspto-grants-2015_10
Patent number
US09163003B2

Reaction notes

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