Potassium Iodide → HCID 54048289, compound

HRID 1954776Notes

Reaction equation

HRID 1954776 reaction equation
[N:1]1([C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:16]=2[CH2:15][C@H:14]([NH:17][C:18](=[O:20])[CH3:19])[CH2:13][CH2:12]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:29](Br)[CH3:30]>CC(C)=O.C(OCC)(=O)C.CCCCCC>[CH2:29]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:16]=2[CH2:15][C@H:14]([NH:17][C:18](=[O:20])[CH3:19])[CH2:13][CH2:12]3)[CH2:2][CH2:3]1)[CH3:30]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 53818849HCID 53818849, compound

Product 1

HCID 54048289HCID 54048289, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a mixture of (R)-N-[8-(piperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]acetamide (100 mg, 0.37 mmol), potassium carbonate (76 mg, 0.54 mmol) and potassium iodide (15 mg, 0.10 mmol) in acetone (20 mL) was added ethyl bromide (56 μL, 0.74 mmol) added and the reaction mixture was vigorously stirred over night. The reaction was filtered and the solvent was evaporated in vacuo. The residue was purified on a silica gel column using chloroform/methanol/concentrated ammonium hydroxide (95:5:0.5) as the eluent. This gave 87 mg (78% yield) of the title compound as an oil which was crystallized from ethyl acetate/hexane. Yield: 55 mg (50%) as white crystals: mp 142-143° C.; [α]21D +27° (c 0.50, chloroform); EIMS (70 eV) m/z (relative intensity) 301 (100, M+).

Workup

  1. additionadded
  2. filtrationThe reaction was filtered
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-21fd5281af73429089b9c8d2097078c8
Source dataset
uspto-grants-2000_09
Patent number
US06124283

Reaction notes

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