Ethanol → HCID 57095169, compound

HRID 704211Notes

Reaction equation

HRID 704211 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)[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([OH:36])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]([NH:32][CH2:4][CH2:3][CH:2]([CH3:6])[CH3:1])=[O:36])[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 3

HCID 702EthanolHCID 7894IsoamylamineHCID 18643025HCID 18643025, compound

Product 1

HCID 57095169HCID 57095169, compound

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 and then concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° 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) at 50° C., 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 (1200 cc) and 35:65 (1.2 liters), collecting 60-cc fractions. Fractions 16 to 33 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C. to give 10-{1-[(2S)-2-hydroxymethyl-1-pyrrolidinyl]-2-propyl}-N-(3-methylbutyl)-2-phenothiazinecarboxamide, L series (0.34 g) in the form of a yellow resin.

Workup

  1. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° 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) at 50° C.
  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 (1200 cc) and 35:65 (1.2 liters)
  8. customcollecting 60-cc fractions
  9. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 50° C.

Sources & evidence

ORD record
ord-638ae8bbb7a841128e34ca79b9499ffc
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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