Methanesulfonic Acid → HCID 22485533, compound

HRID 2181333Notes

Reaction equation

HRID 2181333 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][CH:22]([CH:25]4[CH2:30][CH2:29][N:28]([C:31]5[CH:32]=[CH:33][C:34]([C:37]6[CH:42]=[C:41]([O:43][CH3:44])[C:40]([O:45][CH3:46])=[C:39]([O:47][CH3:48])[CH:38]=6)=[N:35][CH:36]=5)[CH2:27][CH2:26]4)[CH2:21][CH2:20]3)=[CH:15][N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH3:49][S:50]([OH:53])(=[O:52])=[O:51]>CO.C(Cl)(Cl)Cl>[CH3:49][S:50]([OH:53])(=[O:52])=[O:51].[CH3:49][S:50]([OH:53])(=[O:52])=[O:51].[CH3:44][O:43][C:41]1[CH:42]=[C:37]([C:34]2[CH:33]=[CH:32][C:31]([N:28]3[CH2:29][CH2:30][CH:25]([CH:22]4[CH2:21][CH2:20][N:19]([C:16]5[CH:17]=[CH:18][C:13]([C:5]6[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=6)=[N:14][CH:15]=5)[CH2:24][CH2:23]4)[CH2:26][CH2:27]3)=[CH:36][N:35]=2)[CH:38]=[C:39]([O:47][CH3:48])[C:40]=1[O:45][CH3:46]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 22485534HCID 22485534, compound

Product 1

HCID 22485533HCID 22485533, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

To a solution of N,N′-bis[2-(3,4,5-trimethoxyphenyl)-5-pyridyl]-4,4′-bipiperidine (228.0 mg, 0.340 mmol) in methanol-chloroform(1:1, 6.0 mL) was added a 1.0 M aqueous methanesulfonic acid (0.70 mL, 0.70 mmol), and the reaction mixture was concentrated under reduced pressure. Ethanol (5.0 mL) was added to the residue, and the mixture was concentrated under reduced pressure. The residue was recrystallized from methanol-methylene chloride-diethyl ether to yield the title compound as yellow needles (melting point: 226.0-228.0° C.)(170.0 mg, yield: 59%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionEthanol (5.0 mL) was added to the residue
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customThe residue was recrystallized from methanol-methylene chloride-diethyl ether

Sources & evidence

ORD record
ord-a74f6b39dd1c469d989af1d5a2c6d7ac
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

Loading…