Methanol → 1-(3,4,5-Trimethoxybenzoyl)-3-(2-(4-(1-(4-fluorobenzyl)-1h-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-dichlorophenyl)piperidine methanesulfonic acid salt

HRID 323286Notes

Reaction equation

HRID 323286 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:48]=[C:49]([O:53][CH3:54])[C:50]=1[O:51][CH3:52])[C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][CH:27]([NH:30][C:31]3[N:35]([CH2:36][C:37]4[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=4)[C:34]4[CH:44]=[CH:45][CH:46]=[CH:47][C:33]=4[N:32]=3)[CH2:26][CH2:25]2)([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[CH2:9]1)=[O:7].[CH3:55][S:56]([OH:59])(=[O:58])=[O:57].CO.C(OCC)C>C(OCC)(=O)C>[CH3:55][S:56]([OH:59])(=[O:58])=[O:57].[CH3:54][O:53][C:49]1[CH:48]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:50]=1[O:51][CH3:52])[C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([CH2:22][CH2:23][N:24]2[CH2:25][CH2:26][CH:27]([NH:30][C:31]3[N:35]([CH2:36][C:37]4[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=4)[C:34]4[CH:44]=[CH:45][CH:46]=[CH:47][C:33]=4[N:32]=3)[CH2:28][CH2:29]2)([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[CH2:9]1)=[O:7]

Participants

6

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 99623031-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-(4-fluorobenzyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-dichlorophenyl)piperidine

Product 1

HCID 880722841-(3,4,5-Trimethoxybenzoyl)-3-(2-(4-(1-(4-fluorobenzyl)-1h-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-dichlorophenyl)piperidine methanesulfonic acid salt

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Combine 1-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-(4-fluorobenzyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-dichlorophenyl)piperidine (0.54 g) and ethyl acetate (20 mL). Add a solution of methanesulfonic acid (0.14 g) in ethyl acetate (3 mL). After 1 hour concentrate in vacuo to give a residue. Combine the residue and methanol (10 mL) and add diethyl ether (200 mL) to obtain a residue. Decant the supernatant and add diethyl ether to obtain a solid. Collect the solid and dry to give the title compound. HRMS (FAB+): calculated 753.364711. Found 753.366354.

Workup

  1. concentrationAfter 1 hour concentrate in vacuo
  2. customto give a residue
  3. customto obtain a residue
  4. customDecant the supernatant
  5. additionadd diethyl ether
  6. customto obtain a solid
  7. customCollect the solid
  8. customdry

Sources & evidence

ORD record
ord-8b230785f30447bf93896b09d30de4e7
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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