Methyl Acrylate → Methyl 3-[4-(4-Chlorophenyl)-4-fluoropiperidin-1-yl]propionate

HRID 537205Notes

Reaction equation

HRID 537205 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([F:15])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+].[C:21]([O:25][CH3:26])(=[O:24])[CH:22]=[CH2:23]>CO>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([F:15])[CH2:10][CH2:11][N:12]([CH2:23][CH2:22][C:21]([O:25][CH3:26])=[O:24])[CH2:13][CH2:14]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 516892Sodium BicarbonateHCID 674646334-(4-Chlorophenyl)-4-fluoropiperidine hydrochloride

Product 1

HCID 67462732Methyl 3-[4-(4-Chlorophenyl)-4-fluoropiperidin-1-yl]propionateYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-[4-(4-chlorophenyl)-4-fluoropiperidine hydrochloride (280 mg, 1.12 mmol) in methanol (5 mL) was added sodium bicarbonate (500 mg, 5.94 mmol) followed by methyl acrylate (1 mL). The resulting mixture was stirred at room temperature for 14 hours then filtered and concentrated under reduced pressure. The residue was treated with ethyl acetate (10 mL) and the resulting suspension re-filtered and concentrated under reduced pressure. This afforded methyl 3-[4-(4-chlorophenyl)-4-fluoropiperidin-1-yl]propionate as a viscous yellow oil in 94% yield, which was used without further purification.

Workup

  1. filtrationthen filtered
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was treated with ethyl acetate (10 mL)
  4. filtrationthe resulting suspension re-filtered
  5. concentrationconcentrated under reduced pressure
  6. customThis afforded methyl 3-[4-(4-chlorophenyl)-4-fluoropiperidin-1-yl]propionate as a viscous yellow oil in 94% yield, which was used without further purification

Sources & evidence

ORD record
ord-0f8c6c135ebb489a9761ae6f2cb4c78d
Source dataset
uspto-grants-2014_10
Patent number
US08859777B2

Reaction notes

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