Dimethylformamide → HCID 22072638, compound

HRID 1708394Notes

Reaction equation

HRID 1708394 reaction equation
[H-].[Na+].[O:3]=[C:4]1[N:8](C(O)=O)[C:7]2[CH:12]=[CH:13][CH:14]=C[C:6]=2[NH:5]1.[H][H].CI.[CH3:20][N:21]([CH:23]=[O:24])[CH3:22]>>[CH3:20][N:21]1[C:22]2[CH:14]=[CH:13][CH:12]=[CH:7][C:6]=2[N:5]([C:4]([NH2:8])=[O:3])[C:23]1=[O:24]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22028123HCID 22028123, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22072638HCID 22072638, compound

Procedure

80% sodium hydride (0.04 g) was added portionwise to a solution of 2,3-dihydro-2-oxo-1H-benzimidazole-1-carboxylic acid (endo-8-methyl-8azabicyclo[3.2.1]oct-3-yl ester (0.4 g) in dry DMF (10 ml). After hydrogen evolution had subsided methyl iodide (0.082 ml) was added and the reaction mixture was stirred at room temperature for 2 hrs. The solvent was removed under vacuum and the residue was taken up in methylene chloride and washed with water. The organic phase was dried over MgSO4 and concentrated to dryness. Pure title compound was obtained by flash chromatography technique (eluent: methylene chloride/methanol/32% NH4OH 90:10:1) on Silicagel. The oily base was transformed into the hydrochloride salt. 0.21 g M.p. >250° C. MS (C.I.): 316 m/e [M+H]+

Workup

  1. additionwas added
  2. customThe solvent was removed under vacuum
  3. washwashed with water
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-74283db30ad4452895c882b33b771ce1
Source dataset
uspto-grants-1994_10
Patent number
US05358954

Reaction notes

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