Ethyl 4-piperidinecarboxylate → HCID 22111083, compound

HRID 565659Notes

Reaction equation

HRID 565659 reaction equation
Br[CH2:2][C:3]1([CH3:16])[CH2:7][C:6]2[C:8]([CH3:15])=[C:9]([NH2:14])[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]=2[O:4]1.[NH:17]1[CH2:27][CH2:26][CH:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:19][CH2:18]1>C1(C)C(C)=CC=CC=1>[NH2:14][C:9]1[C:10]([CH3:13])=[C:11]([CH3:12])[C:5]2[O:4][C:3]([CH2:2][N:17]3[CH2:27][CH2:26][CH:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:19][CH2:18]3)([CH3:16])[CH2:7][C:6]=2[C:8]=1[CH3:15]

Participants

4

Reactant 2

HCID 70770Ethyl 4-piperidinecarboxylateHCID 108505902-Bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine

Product 1

HCID 22111083HCID 22111083, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
180 °C

Procedure

In an autoclave, a mixture of 2-bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine (8.4 g), ethyl isonipecotate (14 g), and xylene (20 mL) was stirred under nitrogen gas at 180° C. for 15 hours. The supernatant was taken from the reaction mixture and washed with water, saturated aqueous NaHCO3, and saturated aqueous NaCl, dried over MgSO4, treated with activated carbon, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5:1 to 2:1) and crystallized from hexane to provide 2.9 g of the title compound. Yield 27%.

Workup

  1. washwashed with water, saturated aqueous NaHCO3, and saturated aqueous NaCl
  2. dry with materialdried over MgSO4
  3. additiontreated with activated carbon
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5:1 to 2:1)
  7. customcrystallized from hexane

Sources & evidence

ORD record
ord-c1dfce9c7d4d433ab2591f759111d91a
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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