Isopropyl iodide → HCID 69979696, compound

HRID 366528Notes

Reaction equation

HRID 366528 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]=2[C:23]([NH2:25])=[O:24])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH:27]([CH3:29])[CH3:28].[OH-].[K+]>CC(C)=O>[CH2:1]([CH:8]1[CH2:9][CH2:10][N:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH:27]([CH3:29])[CH3:28])[C:15]=2[C:23]([NH2:25])=[O:24])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 14797Potassium HydroxideHCID 53864189HCID 53864189, compound

Product 1

HCID 69979696HCID 69979696, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 200 mg (0.63 mMol) of 4-benzylpiperidinyl-indole-2-carboxamide in 10 ml of acetone was added 321 mg (1.9 mMol) of 2-iodopropane and 106 mg (1.9 mMol) of powdered KOH. The mixture was refluxed for 3 h, then cooled, evaporated and the crude product was purified by silica gel column chromatography using EtOAc:hexane (1:4) to provide the 4-Benzylpiperidinyl-1-(2-propyl)-indole-2-carboxamide as white solids, NMR (DMSO-d6) δ=1.15 (m, 2H), 1.60 (d, 6H), 1.82 (m, 4H), 2.56 (d, 2H), 2.72 (m, 1H), 3.02 (m, 1H), 4.15 (m, 1H), 4.80 (m, 1H), 6.45 (s, 1H), 7.05-7.32 (m, 7H), 7.52 (d, 1H), 7.61 (d, 1H). MS (ESI) m/e 360 (M+).

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. temperaturecooled
  3. customevaporated
  4. customthe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f59ab54665c5427c946848f4aff8a9d0
Source dataset
uspto-grants-2000_10
Patent number
US06130235

Reaction notes

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