Isoamylamine → HCID 57118135, compound

HRID 704200Notes

Reaction equation

HRID 704200 reaction equation
[CH3:1][CH:2]([CH3:6])[CH2:3][CH2:4]N.[OH:7][CH2:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[CH2:14][CH:15]([N:17]1[C:30]2[CH:29]=[C:28]([C:31](=[S:33])[NH2:32])[CH:27]=[CH:26][C:25]=2[S:24][C:23]2[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH3:16]>C(O)C>[OH:7][CH2:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[CH2:14][CH:15]([N:17]1[C:30]2[CH:29]=[C:28]([C:31](=[S:33])[NH:32][CH2:4][CH2:3][CH:2]([CH3:6])[CH3:1])[CH:27]=[CH:26][C:25]=2[S:24][C:23]2[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH3:16]

Participants

4

Reactant 2

HCID 7894IsoamylamineHCID 18643025HCID 18643025, compound

Product 1

HCID 57118135HCID 57118135, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Methylbutylamine (1.74 cc) is added to a solution of 10-{1-[(2S)-2-hydroxymethyl-1-pyrrolidinyl]-2-propyl}-2-phenothiazinecarbothioamide, L series (1.20 g) in absolute ethanol (20 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 40° C. The residue is diluted with ethyl acetate (100 cc), washed with distilled water (2×50 cc), dried over magnesium sulphate and then concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) before being purified by chromatography on a column (height: 14.5 cm; diameter: 2.8 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 65:35 (1.2 liters) and 35:65 (1.2 liters), collecting 60-cc fractions. Fractions 5 to 13 are combined and evaporated under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to give 10-{1-[(2S)-2-hydroxymethyl-1-pyrrolidinyl]-2-propyl}-N-(3-methylbutyl)-2-phenothiazinecarbothioamide, L series (0.64 g) in the form of a yellow resin.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C
  2. additionThe residue is diluted with ethyl acetate (100 cc)
  3. washwashed with distilled water (2×50 cc)
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa)
  6. custombefore being purified by chromatography on a column (height: 14.5 cm; diameter: 2.8 cm) of silica gel (0.04-0.06 mm) with a slight excess pressure of nitrogen (40 kPa)
  7. washeluting with mixtures of cyclohexane and ethyl acetate in proportions (by volume) of 65:35 (1.2 liters) and 35:65 (1.2 liters)
  8. customcollecting 60-cc fractions
  9. customevaporated under reduced pressure (30 mm Hg; 4 kPa) at 40° C.

Sources & evidence

ORD record
ord-b9acca2560924e77ba34de053695f1f3
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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