2-Methylbutylamine → HCID 178446429, compound

HRID 704248Notes

Reaction equation

HRID 704248 reaction equation
[CH3:1][CH:2]([CH2:5][CH3:6])[CH2:3][NH2:4].Cl.[CH2:8]([N:10]([CH2:32][CH3:33])[CH2:11][CH:12]([N:14]1[C:27]2[CH:26]=[C:25]([C:28](=[NH:31])OC)[CH:24]=[CH:23][C:22]=2[S:21][C:20]2[C:15]1=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH3:13])[CH3:9].C(OCC)(=O)C>CO>[CH2:8]([N:10]([CH2:32][CH3:33])[CH2:11][CH:12]([N:14]1[C:27]2[CH:26]=[C:25]([C:28]([NH:4][CH2:3][CH:2]([CH3:1])[CH2:5][CH3:6])=[NH:31])[CH:24]=[CH:23][C:22]=2[S:21][C:20]2[C:15]1=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH3:13])[CH3:9]

Participants

5

Reactant 3

HCID 72832-MethylbutylamineHCID 8857Ethyl AcetateHCID 20074878methyl 10-[(2RS)-1-diethylamino-2-propyl]-2-phenothiazinecarboximidate hydrochloride

Product 1

HCID 178446429HCID 178446429, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of (2RS)-2-methylbutylamine (3.18 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 hydrochloride (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 ethyl acetate (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 a column of neutral alumina (height: 23 cm; diameter: 2.1 cm), eluting with mixtures of ethyl acetate and cyclohexane in proportions (by volume) of 20:80 (850 cc) and 10:90 (500 cc), then with pure ethyl acetate (500 cc) and finally with mixtures of ethyl acetate and methanol in proportions (by volume) of 95:5 (500 cc), 90:10 (500 cc) and 80:20 (500 cc and collecting 50-cc fractions. The first litre is discarded and fractions 40 to 56 are then combined, concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C. to give 10-[(2RS)-1-diethylamino-2-propyl]-N-[ (2RS)-2-methylbutyl]-2-phenothiazinecarboxamidine (1.33 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 a column of neutral alumina (height: 23 cm; diameter: 2.1 cm)
  10. washeluting with mixtures of ethyl acetate and cyclohexane in proportions (by volume) of 20:80 (850 cc) and 10:90 (500 cc)
  11. customwith pure ethyl acetate (500 cc) and finally with mixtures of ethyl acetate and methanol in proportions (by volume) of 95:5 (500 cc), 90:10 (500 cc) and 80:20 (500 cc and collecting 50-cc fractions
  12. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C.

Sources & evidence

ORD record
ord-c602d14a803e47dea7e370c79229bde8
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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