Sodium Iodide → HCID 52952792, compound

HRID 1677723Notes

Reaction equation

HRID 1677723 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=[O:11])=[CH:8][CH:7]=1.[C@@H:15]12[CH2:21][CH2:20][C@@H:19]1[CH2:18][NH:17][CH2:16]2.[I-].[Na+]>>[C@@H:15]12[CH2:21][CH2:20][C@@H:19]1[CH2:18][N:17]([CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=[O:11])=[CH:8][CH:7]=1)[CH2:16]2

Participants

4

Reactant 3

HCID 5238Sodium IodideHCID 144071764-(3-Chloropropoxy)benzamideHCID 67234808HCID 67234808, compound

Product 1

HCID 52952792HCID 52952792, compound

Procedure

To the reaction mixture of Step 1, at ambient temperature, there are added 0.004 mol of (1R,5S)-3-azabicyclo[3.2.0]heptane, the synthesis of which is described in the publication J. Med. Chem. 1967, 10, 621-623, and 0.002 mol of sodium iodide. Heating at reflux is then resumed for 16 hours. The precipitate is filtered off and rinsed with acetonitrile. The filtrate is concentrated to dryness. The residue is taken up in dichloromethane. The resulting solution is extracted with sodium hydroxide solution and then with water, before being dried over magnesium sulphate and concentrated to dryness. The residue is purified by a preparative chromatography technique on a Lichroprep RP-18 phase.

Workup

  1. customthe synthesis of which
  2. temperatureHeating
  3. temperatureat reflux
  4. filtrationThe precipitate is filtered off
  5. washrinsed with acetonitrile
  6. concentrationThe filtrate is concentrated to dryness
  7. extractionThe resulting solution is extracted with sodium hydroxide solution
  8. dry with materialwith water, before being dried over magnesium sulphate
  9. concentrationconcentrated to dryness
  10. customThe residue is purified by a preparative chromatography technique on a Lichroprep RP-18 phase

Sources & evidence

ORD record
ord-991282238d354e4285949bdbd9db7450
Source dataset
uspto-grants-2011_08
Patent number
US08008337B2

Reaction notes

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