Isopropyl iodide → HCID 15925265, compound

HRID 704176Notes

Reaction equation

HRID 704176 reaction equation
[CH2:1]([NH:3][CH2:4][CH:5]([N:7]1[C:20]2[CH:19]=[C:18]([C:21]#[N:22])[CH:17]=[CH:16][C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH3:6])[CH3:2].I[CH:24]([CH3:26])[CH3:25].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH2:1]([N:3]([CH2:4][CH:5]([N:7]1[C:20]2[CH:19]=[C:18]([C:21]#[N:22])[CH:17]=[CH:16][C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH3:6])[CH:24]([CH3:26])[CH3:25])[CH3:2]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 10340Sodium CarbonateHCID 14536548HCID 14536548, compound

Product 1

HCID 15925265HCID 15925265, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of 10-[(2RS)-1-ethylamino-2-propyl]-2-phenothiazinecarbonitrile (4.5 g), 2-iodopropane (7.2 cc) and sodium carbonate (4.6 g) in dry dimethylformamide (60 cc) is heated for 34 hours at a temperature in the region of 150° C. After cooling, the mixture is concentrated to dryness under reduced pressure (5 mm Hg; 0.68 kPa) at 40° C. The residue is taken up with ethyl acetate (200 cc), washed with distilled water (3×100 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual brown oil is purified by chromatography on a column (height: 25 cm; diameter: 4 cm) of silica gel (0.04-0.063 mm) under a slight excess pressure of nitrogen (40 kPa), eluting with a mixture (75:25 by volume) (500 cc) of ethyl acetate and cyclohexane and collecting 60-cc fractions. The combined fractions 3 to 7 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. 10-{(2RS)-1-[N-Ethyl-N-(1-methylethyl)amino]-2-propyl}-2-phenothiazinecarbonitrile (2.37 g) is thereby obtained in the form of an orange oil.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture is concentrated to dryness under reduced pressure (5 mm Hg; 0.68 kPa) at 40° C
  3. washwashed with distilled water (3×100 cc)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  7. customThe residual brown oil is purified by chromatography on a column (height: 25 cm; diameter: 4 cm) of silica gel (0.04-0.063 mm) under a slight excess pressure of nitrogen (40 kPa)
  8. washeluting with a mixture (75:25 by volume) (500 cc) of ethyl acetate and cyclohexane
  9. customcollecting 60-cc fractions
  10. concentrationThe combined fractions 3 to 7 are concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C

Sources & evidence

ORD record
ord-327bf82eb6cc4346b244817476a8d23e
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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