Piperidine → 8-Methoxy-4-piperidino-2,3-dihydrobenzopyran

HRID 65008Notes

Reaction equation

HRID 65008 reaction equation
CS(Cl)(=O)=O.O[CH:7]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([O:17][CH3:18])[C:11]=2[O:10][CH2:9][CH2:8]1.C(N(CC)CC)C.[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>C(Cl)Cl>[CH3:18][O:17][C:16]1[C:11]2[O:10][CH2:9][CH2:8][CH:7]([N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[C:12]=2[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21288997HCID 21288997, compound

Product 1

HCID 212890028-Methoxy-4-piperidino-2,3-dihydrobenzopyran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methane sulfonyl chloride (14.9 ml) is added dropwise to a 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 for 11/2 hours; piperidine (175 ml) is added and the reaction mixture is stirred under nitrogen overnight. The reaction mixture is washed with sat'd aq. sodium bicarbonate, sat'd NaCl, dried, filtered and evaporated in vacuo yielding the desired product as its hydrochloride salt.

Workup

  1. stirringthe reaction mixture is stirred under nitrogen overnight
  2. washThe reaction mixture is washed with sat'd aq. sodium bicarbonate
  3. customdried
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-a456ca6b03e54fb3968ed2f538ff70f5
Source dataset
uspto-grants-1986_09
Patent number
US04612309

Reaction notes

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