Pyridine → HCID 15295461, compound

HRID 2210544Notes

Reaction equation

HRID 2210544 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.Cl[C:28]([O:30][CH3:31])=[O:29]>C(Cl)Cl>[CH3:31][O:30][C:28]([N:18]1[CH2:17][CH2:16][CH:15]([C:9]2[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:8]=2)[CH2:20][CH2:19]1)=[O:29]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 15295460HCID 15295460, compound

Product 1

HCID 15295461HCID 15295461, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 4-(3-cyclopentyloxy-4-methoxyphenyl)piperidine (1.00 mmol, 0.275 g) and pyridine (1.65 mmol, 0.130 g; 133 μL) in dry CH2Cl2 (10 mL) at 0° C. was added methyl chloroformate (1.10 mmol, 0.104 g; 85 μL) dropwise over 5 minutes. The resulting solution was warmed to room temperature and stirred for 1 hour. The reaction was diluted with CH2Cl2 (70 mL) and extracted with water (70 mL). The aqueous phase was extracted with CH2Cl2 (70 mL), the combined organics washed with water (70 mL), dried (Na2SO4) and concentrated in vacuo. The crude oil was purified by flash chromatography (SiO2 : 1) CH2Cl2, 2) 5% EtOAc/CH2Cl2) to afford the title compound as a colorless oil (0.190 g, 57%).

Workup

  1. extractionextracted with water (70 mL)
  2. extractionThe aqueous phase was extracted with CH2Cl2 (70 mL)
  3. washthe combined organics washed with water (70 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude oil was purified by flash chromatography (SiO2 : 1) CH2Cl2, 2) 5% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-1560f5913a45447ebd44366aebb8e76f
Source dataset
uspto-grants-1995_10
Patent number
US05459151

Reaction notes

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