Hydrochloric Acid → HCID 15925248, compound

HRID 704168Notes

Reaction equation

HRID 704168 reaction equation
[CH2:1](N)[CH2:2][CH3:3].[Cl:5][C:6]1[CH:7]=[C:8]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH:20]([CH3:27])[CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[C:15]1[CH:14]=[C:13]([C:28](=[S:30])[NH2:29])[CH:12]=[CH:11][C:10]=1[S:9]2.Cl>C(O)C.C(OCC)(=O)C.C(OCC)C>[Cl:5][C:6]1[CH:7]=[C:8]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH:20]([CH3:27])[CH2:21][N:22]([CH2:23][CH3:24])[CH2:25][CH3:26])[C:15]1[CH:14]=[C:13]([C:28](=[S:30])[NH:29][CH2:1][CH2:2][CH3:3])[CH:12]=[CH:11][C:10]=1[S:9]2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 7852PropylamineHCID 15925247HCID 15925247, compound

Product 1

HCID 15925248HCID 15925248, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

Propylamine (0.75 cc) is added to a solution of 7-chloro-10-[(2RS)-1-diethylamino-2-propyl]-2-phenothiazinecarbothioamide (0.6 g) in absolute ethanol (5 cc). The mixture is brought to 200° C. for 4 hours and then diluted with ethyl acetate (50 cc), washed with distilled water (2×100 cc), dried over magnesium sulphate and then concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual solid is purified by chromatography on a column (height: 8.5 cm; diameter: 2 cm) of silica gel (0.6-0.02 mm), eluting with a 20:80 (by volume) mixture (1.5 liters) of ethyl acetate and cyclohexane, collecting 30-cc fractions. Fractions 25 to 36 are combined and concentrated under reduced pressure (30 mm Hg; 4 kPa) to give a brown oil, which is dissolved in ethyl ether (10 cc). 2.2N ethereal hydrochloric acid (2 cc) is added to this solution. The suspension obtained is filtered to give 7-chloro-10-[(2RS)-1-diethylamino-2-propyl]-N-propyl-2-phenothiazinecarbothioamide (0.06 g), m.p. 130° C.

Workup

  1. washwashed with distilled water (2×100 cc)
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  4. customThe residual solid is purified by chromatography on a column (height: 8.5 cm; diameter: 2 cm) of silica gel (0.6-0.02 mm)
  5. washeluting with a 20:80 (by volume) mixture (1.5 liters) of ethyl acetate and cyclohexane
  6. customcollecting 30-cc fractions
  7. concentrationconcentrated under reduced pressure (30 mm Hg; 4 kPa)
  8. customto give a brown oil, which
  9. customThe suspension obtained
  10. filtrationis filtered

Sources & evidence

ORD record
ord-15a4067a7afc4b35b291a824092832ee
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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