Potassium Carbonate → HCID 22118932, compound

HRID 1275009Notes

Reaction equation

HRID 1275009 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]3)[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Br-:26].[Br-].[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1>ClCCl.CO>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([Br:26])=[C:10]([N:13]3[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]3)[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 22118897HCID 22118897, compoundHCID 53442637Benzyltrimethylammoniumtribromide

Product 1

HCID 22118932HCID 22118932, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred mixture of 1-acetyl-2,3-dihydro-6-(4-methylpiperazin-1-yl)-1H-indole (D11, 2.0 g, 0.0077 mole) and anhydrous potassium carbonate (2.12 g, 0.015 mole) in a mixture of dichloromethane (100 ml) and methanol (50 ml) at -5° C. under argon was treated portionwise over 20 minutes with benzyltrimethylammonium tribromide (3.14 g, 0.0081 mole). The mixture was allowed to warm to room temperature over 1 h, then concentrated in vacuo and the residue dissolved in dichloromethane (150 ml), washed with water (2×100 ml), dried (Na2SO4) and concentrated in vacuo to afford the title compound as a beige solid (2.52 g, 97%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionthe residue dissolved in dichloromethane (150 ml)
  3. washwashed with water (2×100 ml)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-91fb6a36840e40b7a8960da39f7ac606
Source dataset
uspto-grants-2000_12
Patent number
US06159979

Reaction notes

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