Diethyl Ether → HCID 19020564, compound

HRID 1109549Notes

Reaction equation

HRID 1109549 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:7][S:8]([O:11][CH2:12][CH:13]([N:15]1[C:28]2[CH:27]=[C:26]([C:29](=[O:34])[NH:30][CH2:31][CH2:32][CH3:33])[CH:25]=[CH:24][C:23]=2[S:22][C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH3:14])(=[O:10])=[O:9].C(OCC)C>C(#N)C>[CH3:7][S:8]([O-:11])(=[O:10])=[O:9].[CH3:1][N+:2]1([CH2:14][CH:13]([N:15]2[C:28]3[CH:27]=[C:26]([C:29](=[O:34])[NH:30][CH2:31][CH2:32][CH3:33])[CH:25]=[CH:24][C:23]=3[S:22][C:21]3[C:16]2=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH3:12])[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 84541-MethylpyrrolidineHCID 15096228HCID 15096228, compound

Product 1

HCID 19020564HCID 19020564, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

N-Methylpyrrolidine (2.6 cc) is added to a solution of (2RS)-2-[2-(N-propylcarbamoyl)-10-phenothiazinyl)propyl methanesulphonate (2.1 g) in acetonitrile (40 cc). The mixture is brought to reflux for 120 hours. After cooling, the solution obtained is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. to give an oily residue, which is taken up with diethyl ether (50 cc). After one hour's stirring at 20° C., the suspension is filtered and the solid is washed with diethyl ether (3×10 cc) and then dried at 20° C. under reduced pressure (5 mmHg; 0.7 kPa. 1-Methyl-1-{(2RS)-2-[2-(N-propylcarbamoyl)-10-phenothiazinyl]propyl}pyrrolidinium methylsulphonate (2 g) is thereby obtained in the form of an orange-colored solid.

Workup

  1. temperatureto reflux for 120 hours
  2. temperatureAfter cooling
  3. customthe solution obtained
  4. concentrationis concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.
  5. customto give an oily residue, which
  6. filtrationthe suspension is filtered
  7. washthe solid is washed with diethyl ether (3×10 cc)
  8. customdried at 20° C. under reduced pressure (5 mmHg

Sources & evidence

ORD record
ord-ea87f12149554e27b5787200e2699b0e
Source dataset
uspto-grants-1994_06
Patent number
US05321026

Reaction notes

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