Sodium Iodide → HCID 19020548, compound

HRID 1109535Notes

Reaction equation

HRID 1109535 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH2:9]([NH:12][C:13]([C:15]1[CH:28]=[CH:27][C:26]2[S:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([CH:29]([CH3:36])[CH2:30][N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[C:17]=2[CH:16]=1)=[O:14])[CH2:10][CH3:11].[Br:37][CH2:38][C:39]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:40]>C(#N)C>[Br-:37].[C:39]([CH2:38][N+:31]1([CH2:30][CH:29]([N:18]2[C:17]3[CH:16]=[C:15]([C:13](=[O:14])[NH:12][CH2:9][CH2:10][CH3:11])[CH:28]=[CH:27][C:26]=3[S:25][C:24]3[C:19]2=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH3:36])[CH2:35][CH2:34][CH2:33][CH2:32]1)(=[O:40])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 9800851N-propyl-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide

Product 1

HCID 19020548HCID 19020548, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (2.1 g) and sodium iodide (0.1 g) are added to a solution of N-propyl-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide, L series (2.16 g), and 2-bromoacetophenone (2.5 g) in acetonitrile (25 cc), and the mixture is brought to reflux with stirring for 4 hours. After cooling, the reaction mixture is filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue is purified by chromatography on a column (height: 25 cm; diameter: 3.6 cm) of silica gel (0.04-0.063 mm) under a slight excess pressure of nitrogen (40 kPa), eluting successively with a mixture (3 liters) of methylene chloride and methanol (95:5 by volume) and then with a mixture (2 liters) of methylene chloride and methanol (90:10 by volume) and collecting 75-cc fractions. Fractions 39 to 66 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C. The yellow meringue-like residue (0.5 g) is taken up with stirring with isopropyl ether (40 cc) for 1 hour at a temperature in the region of 20° C., drained, washed with isopropyl ether (2×5 cc) and dried under reduced pressure (5 mm Hg; 0.7 kPa) at 40° C. 1-Benzoylmethyl-1-[2-(2-propylcarbamoyl-10-phenothiazinyl)propyl]pyrrolidinium bromide, L series (0.33 g), is thereby obtained in the form of a yellow powder, m.p. about 190° C.

Workup

  1. temperatureto reflux
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture is filtered
  4. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  5. customThe residue is purified by chromatography on a column (height: 25 cm; diameter: 3.6 cm) of silica gel (0.04-0.063 mm) under a slight excess pressure of nitrogen (40 kPa)
  6. washeluting successively with a mixture (3 liters) of methylene chloride and methanol (95:5 by volume)
  7. customwith a mixture (2 liters) of methylene chloride and methanol (90:10 by volume) and collecting 75-cc fractions
  8. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C
  9. stirringwith stirring with isopropyl ether (40 cc) for 1 hour at a temperature in the region of 20° C.
  10. washwashed with isopropyl ether (2×5 cc)
  11. customdried under reduced pressure (5 mm Hg; 0.7 kPa) at 40° C

Sources & evidence

ORD record
ord-7430941ea4494045bb66b07fd7d7541a
Source dataset
uspto-grants-1994_06
Patent number
US05321026

Reaction notes

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