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

HRID 1109527Notes

Reaction equation

HRID 1109527 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][I:30]>CC(C)=O>[I-: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 6328Methyl iodideHCID 9800851N-propyl-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide

Product 1

HCID 190205441-Methyl-1-[2-(2-propylcarbamoyl-10-phenothiazinyl)propyl]pyrrolidinium iodide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of N-propyl-10-[1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide, L series (1.1 g), and methyl iodide (0.75 cc) in acetone (40 cc) is stirred for 2 days at a temperature in the region of 20° C. The pale yellow solution thereby obtained is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C. and the light cream-colored meringue-like residue is suspended with stirring for 30 minutes in diethyl ether (50 cc), drained, washed with diethyl ether (3×10 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 iodide, L series (1.2 g), is thereby obtained in the form of a light beige solid, m.p. 155°-160° C.

Workup

  1. customThe pale yellow solution thereby obtained
  2. concentrationis concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 40° C.
  3. washwashed with diethyl ether (3×10 cc)
  4. customdried at 40° C. under reduced pressure (5 mm Hg; 0.7 kPa)

Sources & evidence

ORD record
ord-af866dc660794bae96545a023c818d6a
Source dataset
uspto-grants-1994_06
Patent number
US05321026

Reaction notes

Loading…