Sodium Carbonate → 10-{1-[N-(Cyclopropylmethyl)-methylamino]-2-propyl}-2-phenothiazinecarbonitrile

HRID 704246Notes

Reaction equation

HRID 704246 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])C.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:30][CH:31]1[CH2:33][CH2:32]1>CN(C)C=O>[CH:33]1([CH2:32][N:3]([CH3:1])[CH2:4][CH:5]([N:7]2[C:20]3[CH:19]=[C:18]([C:21]#[N:22])[CH:17]=[CH:16][C:15]=3[S:14][C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH3:6])[CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 81503BromomethylcyclopropaneHCID 14536548HCID 14536548, compound

Product 1

HCID 5411919910-{1-[N-(Cyclopropylmethyl)-methylamino]-2-propyl}-2-phenothiazinecarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 10-(1-ethylamino-2-propyl)-2-phenothiazinecarbonitrile, L series (3.1 g), sodium carbonate (1.19 g) and bromomethylcyclopropane (2.7 g) in dimethylformamide (32 cc) is heated to 150° C. for 9 hours. After cooling, the reaction mixture is poured into distilled water (300 cc) and extracted with ethyl acetate (3×150 cc). The combined organic phases are washed with distilled water (4×100 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C. The brown oily residue (3.38 g) is purified by chromatography on a column (height: 30 cm; diameter: 2.5 cm) of silica gel (0.06-0.20 mm), eluting with a mixture (80:20 by volume) (2 liters) of methylene chloride 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-{1-[N-(Cyclopropylmethyl)-methylamino]-2-propyl}-2-phenothiazinecarbonitrile, L series (1.83 g) is thereby obtained in the form of a yellow oil.

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture is poured
  3. distillationinto distilled water (300 cc)
  4. extractionextracted with ethyl acetate (3×150 cc)
  5. washThe combined organic phases are washed with distilled water (4×100 cc)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C
  9. customThe brown oily residue (3.38 g) is purified by chromatography on a column (height: 30 cm; diameter: 2.5 cm) of silica gel (0.06-0.20 mm)
  10. washeluting with a mixture (80:20 by volume) (2 liters) of methylene chloride 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-005ce9f8cd0446968ba48311570c76a3
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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