Sodium Iodide → HCID 14426293, compound

HRID 2350923Notes

Reaction equation

HRID 2350923 reaction equation
[CH2:1]([C:3]1[O:7][C:6]([C:8]2([N:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:15](=[O:18])[CH2:16][CH3:17])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:5][N:4]=1)[CH3:2].[CH2:25](Br)[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[Na+].[I-].C([O-])([O-])=O.[Na+].[Na+]>C(#N)C>[C:27]1([CH2:26][CH2:25][N:11]2[CH2:10][CH2:9][C:8]([C:6]3[O:7][C:3]([CH2:1][CH3:2])=[N:4][N:5]=3)([N:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:15](=[O:18])[CH2:16][CH3:17])[CH2:13][CH2:12]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7666Phenethyl bromideHCID 10340Sodium CarbonateHCID 14426227HCID 14426227, compound

Product 1

HCID 14426293HCID 14426293, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(ethyl-1,3,4-oxadiazolyl)-4-(N-phenylpropionamido)piperidine (900 mg, 2.74 mmol), phenethyl bromide (507 mg, 2.74 mmol), NaI (490 mg, 3.3 mmol), Na2CO3 (2.0 g) in acetonitrile (50 ml) was refluxed for 72 hours. It was filtered and concentrated in vacuo. The residue was treated with CH2Cl2 (100 ml) and filtered again. The filtrate was concentrated in vacuo and the resulting residue was chromatographed (SiO2, EtOAc/Hex 1:1) to give the product (904 mg, 2.1 mmol) as a colorless oil: IR (neat) 1660 cm-1 ; NMR (60 MHz, CDCl3) δ0.87 (t, 3H, CH3CH2CON), 1.37 (t, 3H, oxadiazolyl CH3), 1.60-3.15 (m, 16H), 7.23 and 7.50 (2bs, 10H, phenyl H's). ##STR31##

Workup

  1. temperaturewas refluxed for 72 hours
  2. filtrationIt was filtered
  3. concentrationconcentrated in vacuo
  4. additionThe residue was treated with CH2Cl2 (100 ml)
  5. filtrationfiltered again
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe resulting residue was chromatographed (SiO2, EtOAc/Hex 1:1)

Sources & evidence

ORD record
ord-146c25a2f8d24d26a0236ab9fa723654
Source dataset
uspto-grants-1989_10
Patent number
US04871749

Reaction notes

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