Water → HCID 178457511, compound

HRID 704247Notes

Reaction equation

HRID 704247 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].Cl.Cl.[CH2:7]([N:9]([CH2:31][CH3:32])[CH2:10][CH:11]([N:13]1[C:26]2[CH:25]=[C:24]([C:27](=[NH:30])OC)[CH:23]=[CH:22][C:21]=2[S:20][C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH3:12])[CH3:8].O>CO>[CH2:7]([N:9]([CH2:31][CH3:32])[CH2:10][CH:11]([N:13]1[C:26]2[CH:25]=[C:24]([C:27]([NH:4][CH2:1][CH2:2][CH3:3])=[NH:30])[CH:23]=[CH:22][C:21]=2[S:20][C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH3:12])[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 7852PropylamineHCID 15925386methyl 10-[(2RS)-1-diethylamino-2-propyl]-2-phenothiazinecarboximidate dihydrochloride

Product 1

HCID 178457511HCID 178457511, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of propylamine (1.95 cc) in methanol (5 cc) is added dropwise in the course of 5 minutes to a solution, cooled to 0°-5° C., of methyl 10-[(2RS)-1-diethylamino-2-propyl]-2-phenothiazinecarboximidate dihydrochloride (3.49 g) in methanol (21 cc). The mixture is stirred for 2 hours at 5° C. and then concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C. to give a residue which is taken up with distilled water (50 cc). The solution is washed with distilled water (50 cc) alkalinized to pH 9 with N sodium hydroxide. The two phases are allowed to settle and the organic phase is separated and washed with half-saturated (sodium chloride) solution (50 cc), dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C. The residue is purified by chromatography on neutral alumina (height: 20 cm; diameter: 2.1 cm), eluting with pure ethyl acetate (375 cc) and finally with mixtures of ethyl acetate and methanol in proportions (by volume) of 99:1 (375 cc), 98:2 (500 cc), 95:5 (500 cc), 90:10 (500 cc) and 80:20 (500 cc) and collecting 25-cc fractions. Fractions 40 to 70 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C. to give 10-[(2RS)-1-diethylamino-2-propyl]-N-propyl-2-phenothiazinecarboxamidine (1.49 g) in the form of a yellow product of meringue-like consistency.

Workup

  1. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C.
  2. customto give a residue which
  3. washThe solution is washed with distilled water (50 cc)
  4. customthe organic phase is separated
  5. washwashed with half-saturated (sodium chloride) solution (50 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 residue is purified by chromatography on neutral alumina (height: 20 cm; diameter: 2.1 cm)
  10. washeluting with pure ethyl acetate (375 cc) and finally with mixtures of ethyl acetate and methanol in proportions (by volume) of 99:1 (375 cc), 98:2 (500 cc), 95:5 (500 cc), 90:10 (500 cc) and 80:20 (500 cc)
  11. customcollecting 25-cc fractions
  12. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C.

Sources & evidence

ORD record
ord-f842053319c94c47bdb48b2f03294aad
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

Loading…