1,2-Diaminocyclohexane → HCID 15925359, compound

HRID 704218Notes

Reaction equation

HRID 704218 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[NH2:8].[CH3:9][N:10]([CH3:31])[CH2:11][CH:12]([N:14]1[C:27]2[CH:26]=[C:25]([C:28](=S)N)[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]>C(OCC)(=O)C>[CH3:31][N:10]([CH3:9])[CH2:11][CH:12]([N:14]1[C:27]2[CH:26]=[C:25]([C:28]3[NH:8][CH:3]4[CH2:4][CH2:5][CH2:6][CH2:7][CH:2]4[N:1]=3)[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]

Participants

4

Reactant 2

HCID 46101,2-DiaminocyclohexaneHCID 15925238HCID 15925238, compound

Product 1

HCID 15925359HCID 15925359, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

1,2-Diaminocyclohexane (9.3 g) is added to an ethanolic solution (35 cc) of 10-[(2RS)-1-dimethylamino-2-propyl]-2-phenothiazinecarbothioamide (2.8 g). The mixture is heated in an autoclave to 160° C. for 4.5 hours. The reaction mixture is diluted with ethyl acetate (100 cc) and washed with distilled water (3×100 cc). The organic phase is separated after settling has taken place, dried over magnesium sulphate, filtered and evaporated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue is purified by chromatography on a column (height: 22 cm; diameter: 4 cm) of silica gel (0.04-0.06 mm) with a slight excess pressure of nitrogen (40 kPa), eluting with 1,2-dichloroethane (1 liter) and mixtures of 1,2-dichloroethane and methanol in proportions (by volume) of 90:10 (3 liters), 80:20 (2 liters), 70:30 (2 liters) and 50:50 (1 liter) and with pure methanol (1 liter) and collecting 125-cc fractions. Fractions 63 to 80 containing the pure product are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to give 10-[(2RS)-1-dimethylamino-2-propyl]-2-(3a,4,5,6,7,7a-hexahydro-1H-benzimidazol-2-yl)phenothiazine (1.2 g) in the form of a yellow product of meringue-like consistency.

Workup

  1. washwashed with distilled water (3×100 cc)
  2. customThe organic phase is separated after settling
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  6. customThe residue is purified by chromatography on a column (height: 22 cm; diameter: 4 cm) of silica gel (0.04-0.06 mm) with a slight excess pressure of nitrogen (40 kPa)
  7. washeluting with 1,2-dichloroethane (1 liter) and mixtures of 1,2-dichloroethane and methanol in proportions (by volume) of 90:10 (3 liters), 80:20 (2 liters), 70:30 (2 liters) and 50:50 (1 liter) and with pure methanol (1 liter)
  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-18539e8a171844678ef283e072459c96
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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