Butylamine → N-butyl-10-[(2RS)-1-diethylamino-2-propyl]-2-phenothiazinecarbothioamide

HRID 728708Notes

Reaction equation

HRID 728708 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].[CH2:6]([N:8]([CH2:29][CH3:30])[CH2:9][CH:10]([N:12]1[C:25]2[CH:24]=[C:23]([C:26](=[S:28])N)[CH:22]=[CH:21][C:20]=2[S:19][C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH3:11])[CH3:7]>C(O)C>[CH2:1]([NH:5][C:26]([C:23]1[CH:22]=[CH:21][C:20]2[S:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH:10]([CH3:11])[CH2:9][N:8]([CH2:29][CH3:30])[CH2:6][CH3:7])[C:25]=2[CH:24]=1)=[S:28])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 1453651110-(1-Diethylamino-2-propyl)-2-phenothiazinecarbothioamide

Product 1

HCID 14536544N-butyl-10-[(2RS)-1-diethylamino-2-propyl]-2-phenothiazinecarbothioamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

n-Butylamine (2.4 cc) is added to a solution of 10-[(2RS)-1-diethylamino-2-propyl]-2-phenothiazinecarbothioamide (1.86 g) in absolute ethanol (25 cc). The mixture is brought to 150° C. for 16 hours and then concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. The residue obtained is purified by chromatography on a column (height: 17 cm; diameter: 2.6 cm) of silica gel (0.04-0.06 mm) with a slight excess pressure of nitrogen (40 kPa), eluting with mixtures of cyclohexane and ethyl acetate in proportions (by volume) of 90:10 (250 cc), 80:20 (500 cc) and 50:50 (750 cc) and then with pure ethyl acetate (750 cc), collecting 50-cc fractions. Fractions 10 to 18 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to give N-butyl-10-[(2RS)-1-diethylamino-2-propyl]-2-phenothiazinecarbothioamide (0.96 g).

Workup

  1. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  2. customThe residue obtained
  3. customis purified by chromatography on a column (height: 17 cm; diameter: 2.6 cm) of silica gel (0.04-0.06 mm) with a slight excess pressure of nitrogen (40 kPa)
  4. washeluting with mixtures of cyclohexane and ethyl acetate in proportions (by volume) of 90:10 (250 cc), 80:20 (500 cc) and 50:50 (750 cc)
  5. customwith pure ethyl acetate (750 cc), collecting 50-cc fractions
  6. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.

Sources & evidence

ORD record
ord-a868b86390c142639c131d0a28f56794
Source dataset
uspto-grants-1991_09
Patent number
US05049669

Reaction notes

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