Water → HCID 53794738, compound

HRID 457775Notes

Reaction equation

HRID 457775 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([N:12]3[CH2:17][CH2:16][CH:15]([CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:14][CH2:13]3)[NH:9]2)=[CH:5][C:4]=1[C:25]([NH2:27])=[O:26].[H-].[Na+].Cl.[CH2:31]([N:33]([CH2:37][CH3:38])[CH2:34][CH2:35]Cl)[CH3:32].O>CN(C=O)C>[CH2:31]([N:33]([CH2:37][CH2:38][N:9]1[C:10]2[C:6](=[CH:5][C:4]([C:25]([NH2:27])=[O:26])=[C:3]([O:2][CH3:1])[CH:11]=2)[CH:7]=[C:8]1[N:12]1[CH2:13][CH2:14][CH:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:16][CH2:17]1)[CH2:34][CH3:35])[CH3:32]

Participants

6

Reactant 4

HCID 962WaterHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 24758Sodium hydrideHCID 54354203HCID 54354203, compound

Product 1

HCID 53794738HCID 53794738, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.3 g (0.862 mmol) of 6-methoxy-(4-benzylpiperidinyl)-indole-5-carboxamide was dissolved in 20 mL dry DMF. It was cooled in an ice-bath and reacted with 0.12 g NaH (3 mmol, 60% suspension). 0.172 mg (1 mmol) of 2-(diethylamino)-ethylchloride hydrochloride was added and the mixture was stirred for 18 h. The reaction mixture was poured in to water and extracted with dichloromethane (3×75 mL). The combined extract was washed again with water, dried over anhydrous MgSO4, evaporated and purified by silica gel chromatography on a chromatotron using CH2Cl2-Methanol (95:5) to yield 0.22 g of the desired product. It was converted to the HCl salt and lyophilized, M+ 448.

Workup

  1. temperatureIt was cooled in an ice-bath
  2. extractionextracted with dichloromethane (3×75 mL)
  3. extractionThe combined extract
  4. washwas washed again with water
  5. dry with materialdried over anhydrous MgSO4
  6. customevaporated
  7. custompurified by silica gel chromatography on a chromatotron

Sources & evidence

ORD record
ord-58f5c091eba642838ceb72995e7bee6d
Source dataset
uspto-grants-2007_03
Patent number
US07189739B2

Reaction notes

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