Hydrochloric Acid → 3-[4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]benzoic acid hydrochloride

HRID 1691732Notes

Reaction equation

HRID 1691732 reaction equation
C(OC([N:8]([CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=2)[C:31]([OH:33])=[O:32])[CH2:24][CH:23]1[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=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.[ClH:43].O1CCOCC1.Cl>>[ClH:43].[C:11]1([C@H:9]([NH:8][CH2:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=3)[C:31]([OH:33])=[O:32])[CH2:24][CH:23]2[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH3:10])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 204431481,4-Dioxane hydrochlorideHCID 669059473-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]benzoic acid

Product 1

HCID 669062543-[4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]benzoic acid hydrochloride

Procedure

To 99 mg of 3-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]benzoic acid was added 2.0 mL of a 4 M hydrogen chloride/1,4-dioxane solution of hydrochloric acid. After stirring at room temperature for 2 hours, the reaction mixture was concentrated under reduced pressure, and to the obtained residue were added THF and isopropanol, followed by solidification to obtain 76 mg of 3-[4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]benzoic acid hydrochloride as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionto the obtained residue were added THF and isopropanol

Sources & evidence

ORD record
ord-ed49c311cd284a48880325f76b51a5d0
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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