Isoamylamine → HCID 14536616, compound

HRID 728729Notes

Reaction equation

HRID 728729 reaction equation
[CH3:1][CH:2]([CH3:6])[CH2:3][CH2:4][NH2:5].[N:7]1([CH2:13][CH:14]([N:16]2[C:29]3[CH:28]=[C:27]([C:30](=[S:32])N)[CH:26]=[CH:25][C:24]=3[S:23][C:22]3[C:17]2=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH3:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>C(O)C>[CH3:1][CH:2]([CH3:6])[CH2:3][CH2:4][NH:5][C:30]([C:27]1[CH:26]=[CH:25][C:24]2[S:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH:14]([CH3:15])[CH2:13][N:7]3[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]3)[C:29]=2[CH:28]=1)=[S:32]

Participants

4

Reactant 2

HCID 7894IsoamylamineHCID 14536615HCID 14536615, compound

Product 1

HCID 14536616HCID 14536616, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Methylbutylamine (4.65 cc) is added to a solution of 10-[(2RS)-1-piperidino-2-propyl]-2-phenothiazinecarbothioamide (3.07 g) in absolute ethanol (65 cc). The mixture is brought to 150° C. for 16 hours. The reaction mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C. The residue is diluted with ethyl acetate (150 cc), the solution obtained is washed with distilled water (3×50 cc), dried over magnesium sulphate and then concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa), and the residue is purified by chromatography on a column (height: 23.2 cm; diameter: 3.6 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 80:20 (1 liter) and 50:50 (2 liters), collecting 60-cc fractions. Fractions 5 to 13 are combined and concentrated to dryness at 50° C. under reduced pressure (30 mm Hg; 4 kPa) to give N-(3-methylbutyl)-10-[(2RS)-1-piperidino-2-propyl]-2-phenothiazinecarbothioamide (2.49 g).

Workup

  1. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C
  2. additionThe residue is diluted with ethyl acetate (150 cc)
  3. customthe solution obtained
  4. washis washed with distilled water (3×50 cc)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa)
  7. customthe residue is purified by chromatography on a column (height: 23.2 cm; diameter: 3.6 cm) of silica gel (0.04-0.06 mm) with a slight excess pressure of nitrogen (40 kPa)
  8. washeluting with mixtures of cyclohexane and ethyl acetate in proportions (by volume) of 80:20 (1 liter) and 50:50 (2 liters)
  9. customcollecting 60-cc fractions
  10. concentrationconcentrated to dryness at 50° C. under reduced pressure (30 mm Hg; 4 kPa)

Sources & evidence

ORD record
ord-fa43788ddea441e6909ca185a4b1a7a6
Source dataset
uspto-grants-1991_09
Patent number
US05049669

Reaction notes

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