1,4-Dioxane hydrochloride → 2,2-dimethyl-5-[3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidin-1-yl]-5-oxopentanoic acid hydrochloride

HRID 1691682Notes

Reaction equation

HRID 1691682 reaction equation
C(OC([N:8]([CH2:21][CH:22]1[CH:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:26][CH2:25][N:24]([C:34](=[O:43])[CH2:35][CH2:36][C:37]([CH3:42])([CH3:41])[C:38]([OH:40])=[O:39])[CH2:23]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:44].O1CCOCC1>>[ClH:44].[CH3:42][C:37]([CH3:41])([CH2:36][CH2:35][C:34]([N:24]1[CH2:25][CH2:26][CH:27]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:22]([CH2:21][NH:8][C@@H:9]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)[CH3:10])[CH2:23]1)=[O:43])[C:38]([OH:40])=[O:39]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 669064045-[3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidin-1-yl]-2,2-dimethyl-5-oxopentanoic acid

Product 1

HCID 669061552,2-dimethyl-5-[3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidin-1-yl]-5-oxopentanoic acid hydrochloride

Procedure

To 225 mg of the crude 5-[3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidin-1-yl]-2,2-dimethyl-5-oxopentanoic acid was added 2.0 mL of a 4 M hydrogen chloride/1,4-dioxane solution 2.0 mL, followed by stirring at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was then dissolved in THF. Diisopropylether was added dropwise thereto, and the precipitate was isolated by filtration. This was dried under reduced pressure at 50° C. to obtain 170 mg of 2,2-dimethyl-5-[3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpiperidin-1-yl]-5-oxopentanoic acid hydrochloride as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was then dissolved in THF
  3. additionDiisopropylether was added dropwise
  4. customthe precipitate was isolated by filtration
  5. customThis was dried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-3af248a9e14a43ba8eec827367390dc0
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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