Dimethylformamide → HCID 15925261, compound

HRID 704174Notes

Reaction equation

HRID 704174 reaction equation
[CH3:1][NH:2][CH2:3][CH:4]([N:6]1[C:19]2[C:18](C#N)=[CH:17][CH:16]=[CH:15][C:14]=2[S:13][C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH3:5].I[CH:23]([CH3:25])[CH3:24].C(=O)([O-])O.[Na+].[CH3:31][N:32](C)C=O>C(OCC)(=O)C>[CH3:1][N:2]([CH2:3][CH:4]([N:6]1[C:19]2[CH:18]=[C:17]([C:31]#[N:32])[CH:16]=[CH:15][C:14]=2[S:13][C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH3:5])[CH:23]([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6362Isopropyl iodideHCID 516892Sodium BicarbonateHCID 20074866HCID 20074866, compound

Product 1

HCID 15925261HCID 15925261, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 10-[(2RS)-1-methylamino-2-propyl]-phenothiazinecarbonitrile (4.55 g), 2-iodopropane (2 cc) and sodium hydrogen carbonate (1.9 g) in dry dimethylformamide (45.5 cc) is heated for 6 hours to a temperature in the region of 140° C. After cooling, the reaction mixture is diluted with ethyl acetate (200 cc), washed with distilled water (4×30 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The oily yellow residue is purified by chromatography on a column (height: 25 cm; diameter: 4 cm) of silica gel (0.04-0.063 mm) with a slight excess pressure of nitrogen (40 kPa) and with a mixture (97.5:2.5 by volume) (1 liter) of methylene chloride and methanol, and collecting 60-cc fractions. Fractions 4 to 12 are combined and concentrated to dryness under reduced pressure (30 mm Hg; kPa) at 40 ° C. The oily yellow residue (2.9 g) is purified again by chromatography on a column (height: 25 cm; diameter: 4 cm) of silica gel (0.2-0.063 mm), eluting with a mixture (80:20 by volume) (1 liter) of cyclohexane and ethyl acetate and collecting 60-cc fractions. Fractions 4 to 12 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. 10-{(2RS)-1-[N-Methyl-N-(1-methylethyl) amino]-2-propyl}-2-phenothiazinecarbonitrile (2.2 g) is thereby obtained in the form of a yellow oil.

Workup

  1. temperatureAfter cooling
  2. washwashed with distilled water (4×30 cc)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  6. customThe oily yellow residue is purified by chromatography on a column (height: 25 cm; diameter: 4 cm) of silica gel (0.04-0.063 mm) with a slight excess pressure of nitrogen (40 kPa) and with a mixture (97.5:2.5 by volume) (1 liter) of methylene chloride and methanol
  7. customcollecting 60-cc fractions
  8. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; kPa) at 40 ° C
  9. customThe oily yellow residue (2.9 g) is purified again by chromatography on a column (height: 25 cm; diameter: 4 cm) of silica gel (0.2-0.063 mm)
  10. washeluting with a mixture (80:20 by volume) (1 liter) of cyclohexane and ethyl acetate
  11. customcollecting 60-cc fractions
  12. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C

Sources & evidence

ORD record
ord-ef4cbb202ee344ae8711510d4458651a
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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