Dimethylformamide → 2-Methyl-5-methoxy-1-(piperidinylcarbonyl)benzocyclobutene

HRID 2232256Notes

Reaction equation

HRID 2232256 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.[C:7]1([C:15](O)=O)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2C=1.[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.CN([CH:27]=[O:28])C>C(Cl)Cl>[CH3:15][CH:7]1[C:10]2=[CH:9][CH:14]=[C:13]([O:28][CH3:27])[CH:12]=[C:11]2[CH:2]1[C:1]([N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:5]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8082PiperidineHCID 65578Oxalyl chlorideHCID 178524025HCID 178524025, compound

Product 1

HCID 1317150452-Methyl-5-methoxy-1-(piperidinylcarbonyl)benzocyclobutene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (40.9 ml) is added dropwise to a stirred solution of the benzocyclobutene carboxylic acid obtained in the previous step (90.2 g) dissolved in a mixture of DMF (3 ml) and methylene chloride (450 ml). The reaction mixture is stirred at RT overnight and added dropwise to an ice cold solution of piperidine (185 ml) in methylene chloride (450 ml) over a 90-minute period. The reaction mixture is allowed to stir at RT for five hours, washed with aqueous 5% hydrochloric acid, dried, filtered and evaporated affording the desired product as an oil, which is used in the next step without further purification.

Workup

  1. customobtained in the previous step (90.2 g)
  2. stirringto stir at RT for five hours
  3. washwashed with aqueous 5% hydrochloric acid
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-cf216d3aa8b4425ea07a0dfffcfb0098
Source dataset
uspto-grants-1988_11
Patent number
US04788187

Reaction notes

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