Dichloromethane → HCID 49873225, compound

HRID 1618112Notes

Reaction equation

HRID 1618112 reaction equation
[CH3:1][CH:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([NH2:13])=[O:12])[C:5]=2[C:4](=[O:14])[N:3]1[CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.ClCCl.C([BH3-])#N.[Na+]>CO>[CH:5]1([N:18]2[CH2:19][CH2:20][CH:15]([N:3]3[C:4](=[O:14])[C:5]4[C:6]([C:11]([NH2:13])=[O:12])=[CH:7][CH:8]=[CH:9][C:10]=4[CH:2]3[CH3:1])[CH2:16][CH2:17]2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 5003444Sodium cyanoborohydrideHCID 49873315HCID 49873315, compound

Product 1

HCID 49873225HCID 49873225, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 1-methyl-3-oxo-2-(piperidin-4-yl)-2,3-dihydro-1H-isoindole-4-carboxamide (60 mg, 0.19 mmol) in dichloromethane (2 mL) cyclohexanone (147 mg, 0.28 mmol) sodium acetate (32 mg, 0.38 mmol) and methanol (0.3 mL) were added. The resulted solution was stirred at room temperature for 5 hours. Then sodium cyanoborohydride was added and the mixture was stirred overnight. The solvents were removed under reduce pressure and the residue was dissolved in dichloromethane and washed twice with water. The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo and the residue was purified by flash chromatography (dichloromethane/methanol: 95:5) to give the title compound.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred overnight
  3. customThe solvents were removed
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washwashed twice with water
  6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customthe residue was purified by flash chromatography (dichloromethane/methanol: 95:5)

Sources & evidence

ORD record
ord-6c6c239049f84f1c9b735809ad074a45
Source dataset
uspto-grants-2014_07
Patent number
US08765972B2

Reaction notes

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