benzyl 4-(2,3-dichlorophenyl)pyridine-1(4H)-carboxylate → HCID 66632347, compound

HRID 1750118Notes

Reaction equation

HRID 1750118 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[CH:14]=[CH:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH:11]=[CH:10]1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])[CH2:11][CH2:10]1

Participants

3

Reactant 1

HCID 66633946benzyl 4-(2,3-dichlorophenyl)pyridine-1(4H)-carboxylate

Product 1

HCID 66632347HCID 66632347, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
70 °C

Procedure

To a solution of intermediate 45 (7.0 g, 19.5 mmol) in toluene (150 mL) was added RhCl (PPh3)3 (2.1 g, 2.0 mmol) as a slurry in toluene (50 mL). The reaction was subjected to an atmosphere of H2 at 40 psi and heated to 70° C. After 6 h, the reaction was filtered through silica gel and the silica gel was washed with 1:9 EtOAc/toluene. The filtrate was dissolved in toluene, concentrated in vacuo, and purified by flash chromatography on silica gel column (elution with PE/EtOAc=50:1) to give benzyl 4-(2,3-dichlorophenyl)piperidine-1-carboxylate (intermediate 46) (6.8 g, 96%) as an oil. HPLC: 99%, RT 30843 min. MS (ESI) m/z 386.1 [M+NA]+.

Workup

  1. filtrationthe reaction was filtered through silica gel
  2. washthe silica gel was washed with 1:9 EtOAc/toluene
  3. dissolutionThe filtrate was dissolved in toluene
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography on silica gel column (elution with PE/EtOAc=50:1)

Sources & evidence

ORD record
ord-2f7cc9c9e343406f8d1e910690d42f8d
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

Loading…