Diisopropylethylamine → HCID 86751250, compound

HRID 1378497Notes

Reaction equation

HRID 1378497 reaction equation
Cl.Cl.[OH:3][C:4]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)=[CH:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].BrCCC1C2C(=CC=CC=2)C=CC=1.C(N(C(C)C)CC)(C)C>>[OH:3][C:4]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)=[CH:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 1395411-(2-Bromoethyl)naphthaleneHCID 86751251HCID 86751251, compound

Product 1

HCID 86751250HCID 86751250, compound

Conditions

Temperature
60 °C

Procedure

To 10 mL round bottomed flask with a stirring bar and an argon inlet was added 4-(1-(3-hydroxy-1-oxo-3-(3-pyridinyl)-2-propenyl)piperidine dihydrochloride (400mg, 1.31 mmol), 1-(2-bromoethyl)naphthalene (616 mg, 2.62 mmol) dry DMF (5 mL), and diisopropylethylamine (1.74 mL, 10 mmol). This mixture was heated at 60° C. for 24 h. The DMF was removed in vacuo and the residue was dissolved in EtOAc. This solution was washed with saturated aqueous NaHCO3, H2O and brine. Drying (Na2SO4), filtration and removal of the solvent in vacuo gave an orange oil. This material was chromatographed on 30 g of silica gel using 5% 2-propanol in NH3 saturated CHCl3 as eluant. 1-(2-(1-naphthyl)ethyl)-4-(1-(3-hydroxy-1-oxo-3-(3-pyridinyl)-2-propenyl)piperidine was obtained as a white solid.

Workup

  1. customThe DMF was removed in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThis solution was washed with saturated aqueous NaHCO3, H2O and brine
  4. customDrying
  5. filtration(Na2SO4), filtration and removal of the solvent in vacuo
  6. customgave an orange oil
  7. customThis material was chromatographed on 30 g of silica gel using 5% 2-propanol in NH3 saturated CHCl3 as eluant

Sources & evidence

ORD record
ord-abe64eebe40e45008b823c74f77e525a
Source dataset
uspto-grants-1997_09
Patent number
US05668148

Reaction notes

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