Methyl Bromide → 1-Methyl-1-[2-(2-propylcarbamoyl-10-phenothiazinyl)propyl]pyrrolidinium bromide

HRID 1109531Notes

Reaction equation

HRID 1109531 reaction equation
[CH2:1]([NH:4][C:5]([C:7]1[CH:20]=[CH:19][C:18]2[S:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH:21]([CH3:28])[CH2:22][N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[C:9]=2[CH:8]=1)=[O:6])[CH2:2][CH3:3].[CH3:29][Br:30]>CC(C)=O>[Br-:30].[CH3:29][N+:23]1([CH2:22][CH:21]([N:10]2[C:9]3[CH:8]=[C:7]([C:5](=[O:6])[NH:4][CH2:1][CH2:2][CH3:3])[CH:20]=[CH:19][C:18]=3[S:17][C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH3:28])[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 6323Methyl BromideHCID 9800851N-propyl-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide

Product 1

HCID 190205471-Methyl-1-[2-(2-propylcarbamoyl-10-phenothiazinyl)propyl]pyrrolidinium bromide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of N-propyl-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide, L series (5.5 g), in acetone (15 cc) is introduced, dropwise and with stirring during 30 minutes, into a solution of methyl bromide (9.5 g) in acetone (90 cc), and stirring is maintained for 16 hours at a temperature in the region of 20° C. The suspension obtained is filtered and the solid is washed with acetone (3×1 cc), drained and dried at 40° C. under reduced pressure (5 mm Hg; 0.7 kPa). This amorphous white solid (4.8 g) is dissolved in acetonitrile (12 cc) under reflux. The crystals formed after cooling are drained, washed with ice-cold acetonitrile (3×3 cc) and dried at 40° C. under reduced pressure (5 mm Hg; 0.7 kPa). 1-Methyl-1-[2-(2-propylcarbamoyl-10-phenothiazinyl)propyl]pyrrolidinium bromide, L series (2.05 g), is thereby obtained in the form of a crystalline white solid, m.p. 258° C.

Workup

  1. customThe suspension obtained
  2. filtrationis filtered
  3. washthe solid is washed with acetone (3×1 cc)
  4. customdried at 40° C. under reduced pressure (5 mm Hg; 0.7 kPa)
  5. dissolutionThis amorphous white solid (4.8 g) is dissolved in acetonitrile (12 cc)
  6. temperatureunder reflux
  7. customThe crystals formed
  8. temperatureafter cooling
  9. washwashed with ice-cold acetonitrile (3×3 cc)
  10. customdried at 40° C. under reduced pressure (5 mm Hg; 0.7 kPa)

Sources & evidence

ORD record
ord-13770d22fdec4e10b37bf8b97bebc0cc
Source dataset
uspto-grants-1994_06
Patent number
US05321026

Reaction notes

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