Triethylamine → [5-(1-Isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4-methanesulfonyl-piperazin-1-yl)-methanone

HRID 1786481Notes

Reaction equation

HRID 1786481 reaction equation
Cl.Cl.[CH:3]([N:6]1[CH2:11][CH2:10][CH:9]([O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][C:17]([C:22]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[O:23])=[CH:16]3)[CH2:8][CH2:7]1)([CH3:5])[CH3:4].C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>ClCCl>[CH:3]([N:6]1[CH2:7][CH2:8][CH:9]([O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][C:17]([C:22]([N:24]2[CH2:29][CH2:28][N:27]([S:38]([CH3:37])(=[O:40])=[O:39])[CH2:26][CH2:25]2)=[O:23])=[CH:16]3)[CH2:10][CH2:11]1)([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68565070[5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone dihydrochloride

Product 1

HCID 24958929[5-(1-Isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4-methanesulfonyl-piperazin-1-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone dihydrochloride (82 mg, 0.22 mmol) in dichloromethane (2 ml) were added triethylamine (4.2 eq, 0.13 ml) and methanesulfonyl chloride (1.4 eq, 0.02 ml). The mixture was stirred overnight, diluted with dichloromethane and washed with 1N aqueous sodium bicarbonate solution. The phases were separated, the aqueous phase extracted with dichloromethane, and the combined organic phases washed with brine and dried over magnesium sulfate. The crude product was purified by column chromatography on silica gel (1:0 to 5:1 dichloromethane/methanol eluant) to afford the title compound as an off-white solid. MS (m/z): 449.2 (M+H)+.

Workup

  1. washwashed with 1N aqueous sodium bicarbonate solution
  2. customThe phases were separated
  3. extractionthe aqueous phase extracted with dichloromethane
  4. washthe combined organic phases washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe crude product was purified by column chromatography on silica gel (1:0 to 5:1 dichloromethane/methanol eluant)

Sources & evidence

ORD record
ord-adfe3d9336b84d1ba1667c8e82b797e0
Source dataset
uspto-grants-2009_03
Patent number
US07507736B2

Reaction notes

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