Diisopropylethylamine → (1-(9-(1,3-Dioxolan-2-yl)nonyl)piperidin-4-yl)methyl 2-cyclohexyl-2-hydroxy-2-phenylacetate

HRID 1472746Notes

Reaction equation

HRID 1472746 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[O:14][CH2:13][CH2:12][O:11]1.[CH:15]([N:18]([CH:21]([CH3:23])C)[CH2:19][CH3:20])(C)C.Cl.[CH:25]1([C:31]([OH:48])([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:32]([O:34][CH2:35][CH:36]2CCNCC2)=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>C(#N)C.ClCCl>[CH:42]1([C:31]([OH:48])([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:32]([O:34][CH2:35][CH:36]2[CH2:20][CH2:19][N:18]([CH2:15][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]3[O:14][CH2:13][CH2:12][O:11]3)[CH2:21][CH2:23]2)=[O:33])[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 118323182-(8-Bromooctyl)-1,3-dioxolaneHCID 71093351Piperidin-4-ylmethyl 2-cyclohexyl-2-hydroxy-2-phenylacetate hydrochloride

Product 1

HCID 71112453(1-(9-(1,3-Dioxolan-2-yl)nonyl)piperidin-4-yl)methyl 2-cyclohexyl-2-hydroxy-2-phenylacetate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

2-(8-Bromooctyl)-1,3-dioxolane (218 mg, 0.82 mmol) followed by di-isopropylethylamine (361 μL, 2.07 mmol) were added to a solution of piperidin-4-ylmethyl 2-cyclohexyl-2-hydroxy-2-phenylacetate hydrochloride (252 mg, 0.69 mmol) in acetonitrile (4 mL). The reaction mixture was heated at 60° C. for 17 hours. After this time, the reaction was cooled to RT and diluted with dichloromethane. The organic extracts were washed with water, filtered through a hydrophobic frit, and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography eluting with 100% dichloromethane to 40:1 dichloromethane:methanol to afford the title compound that was used without further purification in the next step.

Workup

  1. temperatureAfter this time, the reaction was cooled to RT
  2. washThe organic extracts were washed with water
  3. filtrationfiltered through a hydrophobic frit
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by silica gel column chromatography
  6. washeluting with 100% dichloromethane to 40:1 dichloromethane

Sources & evidence

ORD record
ord-abb3dadeffe54aa9b1150dcb519b36ae
Source dataset
uspto-grants-2015_04
Patent number
US09012644B2

Reaction notes

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