1,2-Diaminocyclohexane → HCID 9932543, compound

HRID 704219Notes

Reaction equation

HRID 704219 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[NH2:8].[N:9]1([CH2:14][CH:15]([N:17]2[C:30]3[CH:29]=[C:28]([C:31](=S)N)[CH:27]=[CH:26][C:25]=3[S:24][C:23]3[C:18]2=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH3:16])[CH2:13][CH2:12][CH2:11][CH2:10]1>C(OCC)(=O)C>[NH:1]1[CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]2[N:8]=[C:31]1[C:28]1[CH:27]=[CH:26][C:25]2[S:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]([CH:15]([CH3:16])[CH2:14][N:9]3[CH2:13][CH2:12][CH2:11][CH2:10]3)[C:30]=2[CH:29]=1

Participants

4

Reactant 2

HCID 46101,2-DiaminocyclohexaneHCID 1453652810-[1-(1-Pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide

Product 1

HCID 9932543HCID 9932543, compoundYield 30.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

1,2-Diaminocyclohexane (9.12 g) is added to an ethanolic solution (32 cc) of 10-[(2RS)-1-(pyrrolidinyl)-2-propyl]-2-phenothiazinecarbothioamide (2.96 g). The mixture is heated in an autoclave to 150° C. for 10 hours. The reaction mixture is diluted with ethyl acetate (150 cc) and washed with distilled water (4×100 cc). The organic phase is separated after settling has taken place, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue is purified by chromatography on a column (height: 23 cm; diameter: 2.5 cm) of FLUKA type 507 C neutral alumina, eluting with 50:50 (by volume) mixtures (1 liter) of cyclohexane and ethyl acetate and collecting 50-cc fractions. Fractions 2 to 15 containing the pure product are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to give 2-(3a,4,5,6,7,7a-hexahydro-1H-benzimidazol-2-yl)-10-[(2RS)-1-(pyrrolidinyl)-2-propyl]phenothiazine (1.07 g) in the form of a brown product of meringue-like consistency.

Workup

  1. washwashed with distilled water (4×100 cc)
  2. customThe organic phase is separated after settling
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  6. customThe residue is purified by chromatography on a column (height: 23 cm; diameter: 2.5 cm) of FLUKA type 507 C neutral alumina
  7. washeluting with 50:50 (by volume)
  8. customcollecting 50-cc fractions
  9. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.

Sources & evidence

ORD record
ord-188fde1cf4a44882bbe0c56533c7face
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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