Diethyl Ether → (r)-1-(3,4,5-Trimethoxybenzoyl)-3-(2-(4-(1-methyl-1h-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-dichlorophenyl)pyrrolidine methanesulfonic acid salt

HRID 323227Notes

Reaction equation

HRID 323227 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:40]=[C:41]([O:45][CH3:46])[C:42]=1[O:43][CH3:44])[C:6]([N:8]1[CH2:12][CH2:11][C@:10]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([NH:29][C:30]3[N:34]([CH3:35])[C:33]4[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=4[N:31]=3)[CH2:25][CH2:24]2)([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:9]1)=[O:7].[CH3:47][S:48]([OH:51])(=[O:50])=[O:49].C(O)(C)C.C(OCC)C>C(OCC)(=O)C>[CH3:47][S:48]([OH:51])(=[O:50])=[O:49].[CH3:46][O:45][C:41]1[CH:40]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:42]=1[O:43][CH3:44])[C:6]([N:8]1[CH2:12][CH2:11][C@:10]([CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH:26]([NH:29][C:30]3[N:34]([CH3:35])[C:33]4[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=4[N:31]=3)[CH2:27][CH2:28]2)([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:9]1)=[O:7]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 3776IsopropanolHCID 6395Methanesulfonic AcidHCID 53998673(R)-1-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-methyl-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-dichlorophenyl)pyrrolidine

Product 1

HCID 88072375(r)-1-(3,4,5-Trimethoxybenzoyl)-3-(2-(4-(1-methyl-1h-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-dichlorophenyl)pyrrolidine methanesulfonic acid salt

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Combine (R)-1-(3,4,5-trimethoxybenzoyl)-3-(2-(4-(1-methyl-1H-benzimidazol-2-yl-amino)piperidin-1-yl)ethyl)-3-(3,4-dichlorophenyl)pyrrolidine (0.3 g) and ethyl acetate (10 mL). Add dropwise, a solution of methanesulfonic acid (0.11 g, 1.1 mmol) in ethyl acetate (2 mL). Evaporate in vacuo to give a residue. Combine the residue and isopropanol (5 mL) and diethyl ether (200 mL). After 18 hours, a solid is obtained. Decant the supernatant and add diethyl ether. Collect the solid and dry in vacuo to give the title compound: mp; 146-160° C.

Workup

  1. additionAdd dropwise
  2. customEvaporate in vacuo
  3. customto give a residue
  4. customa solid is obtained
  5. customDecant the supernatant
  6. additionadd diethyl ether
  7. customCollect the solid
  8. customdry in vacuo

Sources & evidence

ORD record
ord-9f2b9fa0ac114d9791d5026520f5fcc0
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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