Acetone → HCID 69421884, compound

HRID 366526Notes

Reaction equation

HRID 366526 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([C:14]2N[C:16]3[CH:22]=[C:21]([C:23]([NH2:25])=[O:24])[CH:20]=[CH:19][C:17]=3[N:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].I[CH:29]([CH3:31])[CH3:30].[CH3:32]C(C)=O>>[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:18]([CH:29]([CH3:31])[CH3:30])[C:17]3[C:16]([CH:32]=2)=[CH:22][C:21]([C:23]([NH2:25])=[O:24])=[CH:20][CH:19]=3)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 6362Isopropyl iodideHCID 14797Potassium HydroxideHCID 54031537HCID 54031537, compound

Product 1

HCID 69421884HCID 69421884, compoundYield 50%

Procedure

A mixture of 4-benzylpiperidinyl-benzimidazole-5-carboxamide (318 mg, 1 mMol), solid KOH (280 mg, 5 mMol) and 2-iodopropane (1 g, 6 mMol) was refluxed in 20 mL acetone for 20 h. After the removal of acetone in vacuo, the residue was extracted from water with methylene chloride (3×50 mL). The combined extract was dried, evaporated and chromatographed to yield 180 mg (50%) of the desired product. 1HNMR (CDCl3): δ=7.7 (s, 1H); 7.4-7.1 (m, 7H); 4.8-4.6 (m, 1H); 3.0-2.7 (br, m, 4H); 2.6 (d, 2H); 1.8-1.45 (m, 3H); 1.5 (d, 6H); 1.3-1.1 (m, 2H). MS (ESI) m/e 360 (M).

Workup

  1. customAfter the removal of acetone in vacuo
  2. extractionthe residue was extracted from water with methylene chloride (3×50 mL)
  3. extractionThe combined extract
  4. customwas dried
  5. customevaporated
  6. customchromatographed

Sources & evidence

ORD record
ord-32ce983a56764084b7ff2011a99d88df
Source dataset
uspto-grants-2000_10
Patent number
US06130235

Reaction notes

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