Methyl iodide → HCID 19020542, compound

HRID 1109536Notes

Reaction equation

HRID 1109536 reaction equation
[CH3:1][CH:2]([CH3:30])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:21]=[CH:20][C:19]2[S:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH:22]([CH3:29])[CH2:23][N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[C:10]=2[CH:9]=1)=[O:7].[CH3:31][I:32]>CC(C)=O>[I-:32].[CH3:31][N+:24]1([CH2:23][CH:22]([N:11]2[C:10]3[CH:9]=[C:8]([C:6](=[O:7])[NH:5][CH2:4][CH2:3][CH:2]([CH3:30])[CH3:1])[CH:21]=[CH:20][C:19]=3[S:18][C:17]3[C:12]2=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH3:29])[CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 14536608HCID 14536608, compound

Product 1

HCID 19020542HCID 19020542, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of N-(3-methylbutyl)-10-[1-(1-pyrolidinyl)-2-propyl]-2-phenothiazinecarboxamide, L series (1.5 g), and methyl iodide (0.94 cc) in acetone (50 cc) is stirred for 4 days at a temperature in the region of 20° C. The light yellow solution 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 10 minutes in diethyl ether (100 cc), drained, washed with diethyl ether (2×10 cc) and dried at 40° C. under reduced pressure (5 mm Hg, 0.7 kPa). 1-Methyl-1-{2-[2-(3-methylbutyl)carbamoyl-10-phenothiazinyl]propyl}-pyrrolidinium iodide, L series (1.55 g) is thereby obtained in the form of a light beige powder, m.p. about 125°-130° C., the NMR spectrum of which is identical to that of the product of Example 11.

Workup

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

Sources & evidence

ORD record
ord-80d62a3c9a534c99adf6d1c33d23d2b2
Source dataset
uspto-grants-1994_06
Patent number
US05321026

Reaction notes

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