Potassium Iodide → HCID 11949852, compound

HRID 251463Notes

Reaction equation

HRID 251463 reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:21][CH2:20][C:19]3([CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[N:18]=2)=[CH:13][CH:12]=1.Br[CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[CH:28]1([N:24]2[CH2:23][CH2:22][C:19]3([N:18]=[C:17]([C:14]4[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:3]5[CH2:4][CH2:5][CH2:6][CH:2]5[CH3:1])=[CH:16][CH:15]=4)[O:21][CH2:20]3)[CH2:26][CH2:25]2)[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 11950018HCID 11950018, compound

Product 1

HCID 11949852HCID 11949852, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-{4-[3-(2-methyl-1-pyrrolidinyl)propoxy]phenyl}-3-oxa-1,8-diazaspiro[4.5]dec-1-ene 36 (0.11 g, 0.245 mmol) in acetonitrile (4 ml) is placed under an argon atmosphere. Bromocyclopentane (0.039 ml, 0.368 mmol, 1.5 eq), potassium carbonate (0.068 g, 0.49 mmol, 2 eq) and potassium iodide (0.08 g, 0.05 mmol, 0.2 eq) are added and the mixture is stirred at 50° C. overnight. The mixture is then filtered and the filtrate is concentrated under reduced pressure, taken up in dichloromethane, and washed twice with a saturated aqueous solution of ammonium chloride. The aqueous phases are extracted with dichloromethane and the organic extracts are collected together and dried over magnesium sulfate. Dichloromethane is removed under reduced pressure to give 0.086 g of yellow oil. This crude product is purified by chromatography over silica gel (eluent: dichloromethane/ethanol/ammonia 89:10.9:0.1) to afford 0.034 g of 8-cyclopentyl-2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-3-oxa-1,8-diazaspiro[4.5]dec-1-ene 32.

Workup

  1. filtrationThe mixture is then filtered
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. washwashed twice with a saturated aqueous solution of ammonium chloride
  4. extractionThe aqueous phases are extracted with dichloromethane
  5. customthe organic extracts are collected together
  6. dry with materialdried over magnesium sulfate
  7. customDichloromethane is removed under reduced pressure

Sources & evidence

ORD record
ord-719f57d1b9d342d6a210516066bfb3dc
Source dataset
uspto-grants-2011_01
Patent number
US07863450B2

Reaction notes

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