Isobutylamine → 10-[(2RS)-1-diethylamino-2-propyl]-N-(2-methylpropyl)-2-phenothiazinecarbothioamide

HRID 728717Notes

Reaction equation

HRID 728717 reaction equation
[CH2:1](N)[CH:2]([CH3:4])[CH3:3].[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])[NH2:27])[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>[CH2:29]([N:8]([CH2:6][CH3:7])[CH2:9][CH:10]([N:12]1[C:25]2[CH:24]=[C:23]([C:26](=[S:28])[NH:27][CH2:1][CH:2]([CH3:4])[CH3:3])[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])[CH3:30]

Participants

4

Reactant 2

HCID 6558IsobutylamineHCID 1453651110-(1-Diethylamino-2-propyl)-2-phenothiazinecarbothioamide

Product 1

HCID 1453656710-[(2RS)-1-diethylamino-2-propyl]-N-(2-methylpropyl)-2-phenothiazinecarbothioamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Isobutylamine (2.50 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 50° C. The residue obtained is purified by chromatography on a column (height: 16.5 cm; diameter: 2.8 cm) silica gel (0.04-0.06 mm) with a slight excess presof sure of nitrogen (40 kPa), eluting with mixtures of cyclohexane and ethyl acetate in proportions (by volume) of 80:20 (1.5 liters) and 50:50 (1 liter), collecting 50-cc fractions. Fractions 4 to 15 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to give 10-[(2RS)-1-diethylamino-2-propyl]-N-(2-methylpropyl)-2-phenothiazinecarbothioamide (1.3 g).

Workup

  1. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C
  2. customThe residue obtained
  3. customis purified by chromatography on a column (height: 16.5 cm; diameter: 2.8 cm) silica gel (0.04-0.06 mm) with a slight excess presof sure of nitrogen (40 kPa)
  4. washeluting with mixtures of cyclohexane and ethyl acetate in proportions (by volume) of 80:20 (1.5 liters) and 50:50 (1 liter)
  5. customcollecting 50-cc fractions
  6. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.

Sources & evidence

ORD record
ord-7b6b84990ceb45cdbcfeb59f1d89c308
Source dataset
uspto-grants-1991_09
Patent number
US05049669

Reaction notes

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