Diisopropyl Ether → 2-[3-(3-fluorophenyl)-4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)piperidin-1-yl]-1H-benzimidazole-6-carboxylic acid dihydrochloride

HRID 1691746Notes

Reaction equation

HRID 1691746 reaction equation
C(OC([N:8]([CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]2[NH:32][C:31]3[CH:33]=[C:34]([C:37]([OH:39])=[O:38])[CH:35]=[CH:36][C:30]=3[N:29]=2)[CH2:24][CH:23]1[C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[CH:41]=1)[C@@H:9]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[CH3:10])=O)(C)(C)C.C(OC(C)C)(C)C.[ClH:54].O1CCOCC1>>[ClH:54].[ClH:54].[F:46][C:42]1[CH:41]=[C:40]([CH:23]2[CH:22]([CH2:21][NH:8][C@@H:9]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=[CH:13][CH:12]=3)[CH3:10])[CH2:27][CH2:26][N:25]([C:28]3[NH:32][C:31]4[CH:33]=[C:34]([C:37]([OH:39])=[O:38])[CH:35]=[CH:36][C:30]=4[N:29]=3)[CH2:24]2)[CH:45]=[CH:44][CH:43]=1

Participants

4

Reactant 3

HCID 7914Diisopropyl EtherHCID 204431481,4-Dioxane hydrochlorideHCID 669063102-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-(3-fluorophenyl)piperidin-1-yl]-1H-benzimidazole-6-carboxylic acid

Product 1

HCID 669065042-[3-(3-fluorophenyl)-4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)piperidin-1-yl]-1H-benzimidazole-6-carboxylic acid dihydrochloride

Procedure

A solution of 19 mg of 2-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-(3-fluorophenyl)piperidin-1-yl]-1H-benzimidazole-6-carboxylic acid in 1.00 mL of 4 M hydrogen chloride/1,4-dioxane solution was stirred at room temperature for 2 hours. Diisopropyl ether was added thereto, and the resulting precipitate was collected by filtration, and dried under reduced pressure to obtain 15 mg of 2-[3-(3-fluorophenyl)-4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)piperidin-1-yl]-1H-benzimidazole-6-carboxylic acid dihydrochloride.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-7fe37267b0484973a82b8fa4ba6d3b96
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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