Sodium Iodide → HCID 14426228, compound

HRID 2350924Notes

Reaction equation

HRID 2350924 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].[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[CH2:30][CH2:31]Cl.[Na+].[I-].C([O-])([O-])=O.[Na+].[Na+]>C(#N)C>[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[CH2:30][CH2:31][N:11]1[CH2:10][CH2:9][C:8]([C:6]2[O:7][C:3]([CH2:1][CH3:2])=[N:4][N:5]=2)([N:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15](=[O:18])[CH2:16][CH3:17])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 114124562-(2-chloroethyl)thiopheneHCID 14426227HCID 14426227, compound

Product 1

HCID 14426228HCID 14426228, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(ethyl-1,3,4-oxadiazolyl)-4-(N-phenylpropionamido)piperidine (880 mg, 2.68 mmol), 2-(2-thienyl)ethyl chloride (385 mg, 2.63 mmol), NaI (470 mg, 3.1 mmol) and Na2CO3 (2.0 g) in acetonitrile (50 ml) was refluxed for 72 hours. It was cooled down to room temperature and filtered. The filtrate was concentrated in vacuo and the residue was treated with CH2Cl2 (100 ml). The resulting mixture was filtered and the filtrate was concentrated in vacuo. The residue was chromatographed to give the product (940 mg, 2.14 mmol) as an amber oil: IR (neat) 1660 cm-1 ; NMR (60 MHz, CDCl3) δ0.88 (t, 3H, CH3CH2CO), 1.39 (t, 3H, oxadiazolyl CH3), 1.60 to 3.20 (m, 16H), 6.70 to 7.40 (m, 3H, thienyl H's) 7.44 (s, 5 H, phenyl H's). ##STR33##

Workup

  1. temperaturewas refluxed for 72 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. additionthe residue was treated with CH2Cl2 (100 ml)
  5. filtrationThe resulting mixture was filtered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was chromatographed

Sources & evidence

ORD record
ord-45b6b1f923264b7ba04f7da3e373c4f0
Source dataset
uspto-grants-1989_10
Patent number
US04871749

Reaction notes

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