Sodium Hydroxide → 5-(3,4-dihydropyran-4-yl)-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

HRID 609733

Reaction equation

HRID 609733 reaction equation
[OH-].[Na+].[O:3]1[CH:8]=[CH:7][CH:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14](C(=O)C2C=CC=CC=2)[CH:13]=[C:12]3[CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])[CH2:5][CH2:4]1>CO>[NH3:14].[O:3]1[CH:4]=[CH:5][CH:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[C:12]3[CH2:26][CH2:27][N:28]([CH3:29])[CH3:30])[CH2:7][CH2:8]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 196004485-(3,4-dihydropyran-4-yl)-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole

Product 2

HCID 222AmmoniaYield 10%HCID 196004255-(3,4-dihydropyran-4-yl)-3-[2-(N,N-dimethylamino)ethyl]-1H-indoleYield 141.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous solution of sodium hydroxide (2M, 1 mL, 2 mmol) was added to 5-(3,4-dihydropyran-4-yl)-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole (30 mg, 0.08 mmol) in methanol (2 mL) and the resulting solution was stirred at room temperature for 16 h. The reaction mixture was partitioned between water and ethyl acetate, washed with brine, dried over sodium sulfate and the solvent was removed in vacuo. Preparative thin layer chromatography (silica gel, 10% 2M methanolic ammonia in dichloromethane) yielded 5-(3,4-dihydropyran-4-yl)-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (15.3 mg, 70%); HRMS-FAB+ for C17H22N2O: calculated MH+ :271.18103; found MH+ :271.18177.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f7644bf8f2e14e5d9929e4671f6fde81
Source dataset
uspto-grants-1999_12
Patent number
US05998438

Linked notes

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