Sodium Iodide → HCID 19894627, compound

HRID 893009Notes

Reaction equation

HRID 893009 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[N:9]1([C:14]2[N:19]=[C:18]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[N:17]=[C:16]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[N:15]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[N:9]1([C:14]2[N:15]=[C:16]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[N:17]=[C:18]([N:20]3[CH2:25][CH2:24][N:23]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8])[CH2:22][CH2:21]3)[N:19]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 779706-Bromo-1-hexanolHCID 6497452-(Piperazin-1-yl)-4,6-di(pyrrolidin-1-yl)-1,3,5-triazine

Product 1

HCID 19894627HCID 19894627, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 6-bromohexanol (0.905 g), 2,6-bis(1-pyrrolidinyl)-4-(1-piperazinyl)-1,3,5-triazine (PCT 86/01797, PREPARATION A-45, 1.517 g), potassium carbonate (0.346 g) and sodium iodide (0.075 g) in acetonitrile (165 ml) are stirred under reflux for 4.5 hr. The mixture is concentrated and the residue is partitioned between methylene chloride and potassium bicarbonate (1N). The phases are separated, the organic phase is washed with water and saline, then filtered through sodium sulfate and concentrated. The residue is chromatographed on silica gel (230 g) packed in methanol/methylene chloride (5/95). Elution is performed with 5% methanol/methylene chloride (3 l) followed by 10% methanol/methylene chloride (2 l). 50 ml fractions are collected, fractions 61-78 are pooled and concentrated to give the title compound.

Workup

  1. temperatureunder reflux for 4.5 hr
  2. concentrationThe mixture is concentrated
  3. customthe residue is partitioned between methylene chloride and potassium bicarbonate (1N)
  4. customThe phases are separated
  5. washthe organic phase is washed with water and saline
  6. filtrationfiltered through sodium sulfate
  7. concentrationconcentrated
  8. customThe residue is chromatographed on silica gel (230 g)
  9. washElution
  10. custom50 ml fractions are collected
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-cc1a357c39ef4b63b756a4f1a5a4a5fc
Source dataset
uspto-grants-1992_06
Patent number
US05120843

Reaction notes

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