Propylamine → HCID 15925260, compound

HRID 704173Notes

Reaction equation

HRID 704173 reaction equation
[ClH:1].[CH3:2][N:3]([CH2:7][CH:8]([N:10]1[C:23]2[CH:22]=[C:21]([C:24](=[S:26])[NH2:25])[CH:20]=[CH:19][C:18]=2[S:17][C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH3:9])[CH:4]([CH3:6])[CH3:5].[CH2:27](N)[CH2:28][CH3:29]>C(O)C>[ClH:1].[CH3:2][N:3]([CH2:7][CH:8]([N:10]1[C:23]2[CH:22]=[C:21]([C:24](=[S:26])[NH:25][CH2:27][CH2:28][CH3:29])[CH:20]=[CH:19][C:18]=2[S:17][C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH3:9])[CH:4]([CH3:5])[CH3:6]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 15925258HCID 15925258, compound

Product 1

HCID 15925260HCID 15925260, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 10-{(2RS)-1-[N-methyl-N-(1-methylethyl)amino]-2-propyl}-2-phenothiazinecarbothioamide hydrochloride (1.6 g) and propylamine (4.8 cc) in absolute ethanol (32 cc) is heated for 16 hours at a temperature in the region of 100° C. After cooling, the mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue is dissolved in ethyl ether (100 cc) and the solution obtained is washed with N aqueous sodium hydroxide solution (4 cc) and then with saturated aqueous sodium chloride solution (2×10 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual red-brown gum is purified by chromatography on a column (height: 25 cm; diameter: 3 cm) of silica gel (0.04-0.063 mm) with a slight excess pressure of nitrogen (40 kPa), eluting with a mixture (97:3 by volume) (1 liter) of methylene chloride and methanol and collecting 60-cc fractions. Fractions 6 to 12 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residual yellow oil (0.85 g) is dissolved in ethyl ether (50 cc) in the presence of charcoal 3S. The mixture is filtered and a 3N solution (1 cc of hydrochloric acid in ethyl ether is added to the yellow filtrate, and the mixture is stirred for 1 hour at a temperature in the region of 20° C. The solid formed is drained washed with ethyl ether (5 cc) and dried under reduced pressure (5 mm Hg; 0.68 kPa) at 40° C. 10-{(2RS)-1-[N-Methyl-N-(1-methylethyl)amino]-2-propyl}-N-propyl-2-phenothiazinecarbothioamide hydrochloride (0.58 g) is thereby obtained in the form of a yellow solid, m.p. about 140° C. (melts forming a a paste).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  3. dissolutionThe residue is dissolved in ethyl ether (100 cc)
  4. customthe solution obtained
  5. washis washed with N aqueous sodium hydroxide solution (4 cc)
  6. dry with materialwith saturated aqueous sodium chloride solution (2×10 cc), dried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  9. customThe residual red-brown gum is purified by chromatography on a column (height: 25 cm; diameter: 3 cm) of silica gel (0.04-0.063 mm) with a slight excess pressure of nitrogen (40 kPa)
  10. washeluting with a mixture (97:3 by volume) (1 liter) of methylene chloride and methanol
  11. customcollecting 60-cc fractions
  12. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  13. dissolutionThe residual yellow oil (0.85 g) is dissolved in ethyl ether (50 cc) in the presence of charcoal 3S
  14. filtrationThe mixture is filtered
  15. additiona 3N solution (1 cc of hydrochloric acid in ethyl ether is added to the yellow filtrate
  16. customThe solid formed
  17. washis drained washed with ethyl ether (5 cc)
  18. customdried under reduced pressure (5 mm Hg; 0.68 kPa) at 40° C

Sources & evidence

ORD record
ord-dd6b5fc7eb8c40fbb141204cda77ee87
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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