Piperidine → 7-Methoxy-3-piperidino-2,2-dimethylbenzofuran

HRID 65011Notes

Reaction equation

HRID 65011 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][C:9]([CH3:13])([CH3:12])[CH:8](O)[C:7]=2[CH:6]=[CH:5][CH:4]=1.CS(Cl)(=O)=O.[NH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[C:11]2[O:10][C:9]([CH3:13])([CH3:12])[CH:8]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 141266487-Methoxy-3-hydroxy-2,2-dimethylbenzofuran

Product 1

HCID 141266497-Methoxy-3-piperidino-2,2-dimethylbenzofuran

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (29 ml) is added to a stirred solution of the product obtained in Step 4. (25.4 g) in methylene chloride (560 ml) at RT under nitrogen. Methanesulfonyl chloride (11.1 ml) is added dropwise to the mixture which is cooled to 0° C. The mixture is stirred for 3 hours at RT, cooled to 0° C., piperidine (128 ml) added and stirring continued at RT overnight. Sat'd aq. sodium bicarbonate is added to the mixture, the phases separated and the organic phase washed with sodium bicarbonate, sat'd NaCl, dried, filtered and evaporated in vacuo. The residue is dissolved in toluene and evaporated in vacuo affording the desired product as the hydrochloride salt.

Workup

  1. customat RT
  2. temperaturecooled to 0° C.
  3. stirringstirring
  4. waitcontinued at RT overnight
  5. customthe phases separated
  6. washthe organic phase washed with sodium bicarbonate
  7. customdried
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. dissolutionThe residue is dissolved in toluene
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-7c9f1baf340b45f78fb22d4fcfb52a35
Source dataset
uspto-grants-1986_09
Patent number
US04612309

Reaction notes

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