2-(2-Chloroethyl)-1-methylpyrrolidine → HCID 22291035, compound

HRID 1369554Notes

Reaction equation

HRID 1369554 reaction equation
Cl[CH2:2][CH2:3][CH:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH3:9].[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:31])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[CH:20]=2)=[CH:13][C:12]=1[NH:32][C:33](=[O:41])[C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([OH:40])[CH:35]=1>>[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:31])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)[CH:20]=2)=[CH:13][C:12]=1[NH:32][C:33](=[O:41])[C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH:8]2[CH2:2][CH2:3][CH2:4][N:5]([CH3:9])[CH2:6][CH2:7]2)[CH:35]=1

Participants

3

Reactant 2

HCID 2850932-(2-Chloroethyl)-1-methylpyrrolidineHCID 22291011HCID 22291011, compound

Product 1

HCID 22291035HCID 22291035, compound

Procedure

As described hereinbefore in Example 7, 2-(2-chloroethyl)-N-methylpyrrolidine was reacted with N-[2-methyl-5-(3-morpholinobenzamido)phenyl]-3-hydroxybenzamide and the reaction product was purified by column chromatography on silica using a 9:1 mixture of methylene chloride and methanol as eluent. There was thus obtained N-[2-methyl-5-(3-morpholinobenzamido)phenyl]-3-[2-(N-methylpyrrolidin-2-yl)ethoxy]benzamide (Example 7, Compound No. 32). On further elution an isomeric by-product was obtained. There was thus obtained the title compound NMR Spectrum: (DMSOd6) 1.6 (m, 1H), 1.79 (m, 3H), 2.04 (m, 2H), 2.17 (s, 3H), 2.24 (s, 3H), 2.52 (m, 4H), 3.18 (t, 4H), 3.76 (t, 4H), 4.66 (m, 1H), 7.1 (m, 2H), 7.21 (d, 1H), 7.4 (m, 4H), 7.5 (d, 1H), 7.56 (m, 1H), 7.78 (d, 1H), 9.83 (s, 1H), 10.11 (s, 1H); Mass Spectrum: M+H+543.

Workup

  1. customthe reaction product was purified by column chromatography on silica using
  2. additiona 9:1 mixture of methylene chloride and methanol as eluent
  3. washOn further elution an isomeric by-product
  4. customwas obtained

Sources & evidence

ORD record
ord-6121f672cd2243b88b2ade4589dd1fa7
Source dataset
uspto-grants-2003_06
Patent number
US06579872B1

Reaction notes

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