Ethylamine → HCID 14536548, compound

HRID 704177Notes

Reaction equation

HRID 704177 reaction equation
CS(O[CH2:6][CH:7]([N:9]1[C:22]2[CH:21]=[C:20]([C:23]#[N:24])[CH:19]=[CH:18][C:17]=2[S:16][C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH3:8])(=O)=O.[CH2:25]([NH2:27])[CH3:26]>C1(C)C=CC=CC=1>[CH2:25]([NH:27][CH2:6][CH:7]([N:9]1[C:22]2[CH:21]=[C:20]([C:23]#[N:24])[CH:19]=[CH:18][C:17]=2[S:16][C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH3:8])[CH3:26]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 145021392-(2-Cyano-10-phenothiazinyl)propyl mesylate

Product 1

HCID 14536548HCID 14536548, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (2RS)-2-(2-cyano-10-phenothiazinyl)-propyl methanesulphonate (50 g) and ethylamine (100 cc) in toluene (600 cc) is heated for 24 hours to a temperature in the region of 105° C. After cooling, the mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue is taken up with distilled water (250 cc) and the mixture is extracted successively with ethyl acetate (500 cc and 250 cc). The combined organic phases are extracted with N aqueous hydrochloric acid solution (2×500 cc). The aqueous phases are alkalinized with caustic soda (d=1.33) to pH 13 and extracted successively with ethyl acetate (500 cc and 250 cc). The combined organic phases are washed with saturated aqueous sodium chloride solution (250 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. 10-[(2RS)-1-Ethylamino-2-propyl]-2-phenothiazinecarbonitrile (30.4 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 (30 mm Hg; 4 kPa) at 40° C
  3. extractionthe mixture is extracted successively with ethyl acetate (500 cc and 250 cc)
  4. extractionThe combined organic phases are extracted with N aqueous hydrochloric acid solution (2×500 cc)
  5. extractionextracted successively with ethyl acetate (500 cc and 250 cc)
  6. washThe combined organic phases are washed with saturated aqueous sodium chloride solution (250 cc)
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C

Sources & evidence

ORD record
ord-a651dcd0ece446a991212a969555b2b6
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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