Ethyl Acetate → HCID 14536540, compound

HRID 704189Notes

Reaction equation

HRID 704189 reaction equation
S(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)C.C(O[CH2:29][CH3:30])(=O)C>>[N:9]1([CH2:6][CH:7]([N:9]2[C:22]3[CH:21]=[C:20]([C:23]#[N:24])[CH:19]=[CH:18][C:17]=3[S:16][C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH3:8])[CH2:30][CH2:29][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 145021392-(2-Cyano-10-phenothiazinyl)propyl mesylate

Product 1

HCID 14536540HCID 14536540, compound

Procedure

A solution of 2-(2-cyano-10-phenothiazinyl)propyl mesylate (9.05 g) in hexamethylenimine (28.2 cc) is brought to 90° C. for 16 hours. After cooling, the mixture is diluted with ethyl acetate (200 cc) and washed with distilled water (4×150 cc). The organic phase is dried over magnesium sulphate, 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 of 0.06-0.2 mm silica gel (height: 44 cm; diameter: 3.8 cm), eluting with mixture of cyclohexane and ethyl acetate in proportions (by volume) of 80:20 (500 cc) and 70:30 (1500 cc) and collecting 125-cc fractions. Fractions 7 to 15 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to give 10-[(2RS)-1-(perhydro-1-azepinyl)-2-propyl]-2-phenothiazinecarbonitrile (5.27 g) in the form of a yellow product of honey-like consistency.

Workup

  1. temperatureAfter cooling
  2. washwashed with distilled water (4×150 cc)
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  6. customThe residue is purified by chromatography on a column of 0.06-0.2 mm silica gel (height: 44 cm; diameter: 3.8 cm)
  7. washeluting with mixture of cyclohexane and ethyl acetate in proportions (by volume) of 80:20 (500 cc) and 70:30 (1500 cc)
  8. customcollecting 125-cc fractions
  9. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.

Sources & evidence

ORD record
ord-88087ad13b844e9fb5b39c2eab3f3c09
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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