Potassium Iodide → 6-Acetylamino-1-[N-(4-cyclohexylbutan-1-yl)-N-methylaminomethyl]indan

HRID 1740876Notes

Reaction equation

HRID 1740876 reaction equation
[C:1]([NH:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH:11]2[CH2:14][NH:15][CH3:16])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].S(O[CH2:22][CH2:23][CH2:24][CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)(=O)(=O)C.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(CC(C)=O)C>[C:1]([NH:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH:11]2[CH2:14][N:15]([CH2:22][CH2:23][CH2:24][CH2:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH3:16])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 103767534-Cyclohexylbutan-1-ol mesylateHCID 218342106-Acetylamino-1-(N-methylaminomethyl)indan

Product 1

HCID 218342366-Acetylamino-1-[N-(4-cyclohexylbutan-1-yl)-N-methylaminomethyl]indan

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 6-Acetylamino-1-(N-methylaminomethyl)indan (1.5 g), 4-cyclohexylbutan-1-ol mesylate (2.5 g), potassium carbonate (1.4 g), and a crystal of potassium iodide in MIBK (80 ml) were refluxed for 5 h. After cooling inorganic salts were filtered off and the solvent evaporated in vacuo. The remaining oil was subjected to column chromatography on SiO2 (eluted with ethyl acetate: heptane: triethylamine 80:20:4). The free base of the title compound was isolated as an oil. The sesquioxalate of 13a crystallized from acetone. Yield 1.6 g Mp: 145-155° C.

Workup

  1. temperatureAfter cooling inorganic salts
  2. filtrationwere filtered off
  3. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-3b420eefaa4f4ba4ba22be7391d00899
Source dataset
uspto-grants-1999_10
Patent number
US05972964

Reaction notes

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