Piperidine → 6-Methoxy-4-piperidino-2,3-dihydrobenzopyran

HRID 65005Notes

Reaction equation

HRID 65005 reaction equation
CS(Cl)(=O)=O.[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[O:16][CH2:15][CH2:14][CH:13](O)[C:12]=2[CH:18]=1.[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(N(CC)CC)C>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[O:16][CH2:15][CH2:14][CH:13]([N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[C:12]=2[CH:18]=1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 13712845HCID 13712845, compound

Product 1

HCID 137128466-Methoxy-4-piperidino-2,3-dihydrobenzopyran

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Methane sulfonyl chloride (14.9 ml) is added dropwise to a stirred solution of the product obtained in Step 1. (31.6 g) and triethylamine (29.3 ml) in methylene chloride (750 ml) cooled to 0° C. under nitrogen. The reaction mixture is stirred at RT for 21/2 hours and cooled to 0° C. Piperidine (175 ml) is added to the cooled reaction mixture and the solution stirred at RT overnight. Sat'd aq. sodium bicarbonate is added to the solution and the mixture is stirred for 30 minutes. The organic layer is separated, washed with sat'd NaCl and dried. The solution is filtered and the filtrate evaporated in vacuo yielding the desired product as its hydrochloride salt.

Workup

  1. temperaturecooled to 0° C
  2. stirringthe solution stirred at RT overnight
  3. stirringthe mixture is stirred for 30 minutes
  4. customThe organic layer is separated
  5. washwashed with sat'd NaCl
  6. customdried
  7. filtrationThe solution is filtered
  8. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-47f25a827f0649069412c925bd547949
Source dataset
uspto-grants-1986_09
Patent number
US04612309

Reaction notes

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