Dichloromethane → HCID 22041832, compound

HRID 1791070Notes

Reaction equation

HRID 1791070 reaction equation
C1C2C(COC([NH:18][C:19]3[CH:28]=[C:27]4[C:22]([CH:23]=[CH:24][C:25]([C:29]([NH:31][C:32]5[CH:33]=[C:34]([CH:39]=[CH:40][CH:41]=5)[C:35]([O:37][CH3:38])=[O:36])=[O:30])=[CH:26]4)=[CH:21][CH:20]=3)=O)C3C(=CC=CC=3)C=2C=CC=1.ClCCl.N1CCCCC1>C1COCC1>[NH2:18][C:19]1[CH:28]=[C:27]2[C:22]([CH:23]=[CH:24][C:25]([C:29]([NH:31][C:32]3[CH:33]=[C:34]([CH:39]=[CH:40][CH:41]=3)[C:35]([O:37][CH3:38])=[O:36])=[O:30])=[CH:26]2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 8082PiperidineHCID 22041853HCID 22041853, compound

Product 1

HCID 22041832HCID 22041832, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 380 mg (0.70 mmol) of compound 109 was added 30 mL of dichloromethane, 3 mL of THF and 1 mL of piperidine. The resulting clear solution was allowed to stir for 3 hours. Then, the reaction was extracted with ethyl acetate and 1N HCl (aqueous). The dried organic layer (magnesium sulfate) was filtered and the volatiles removed in vacuo. The resulting residue was dissolved in dichloromethane and 3 mL of 1 N HCl in diethyl ether and 50 mL of diethyl ether were added to form a precipitate that was collected by vacuum filtration. After drying, this provided 212 mg of compound 111 as the hydrochloride salt.

Workup

  1. extractionThen, the reaction was extracted with ethyl acetate and 1N HCl (aqueous)
  2. filtrationThe dried organic layer (magnesium sulfate) was filtered
  3. customthe volatiles removed in vacuo
  4. dissolutionThe resulting residue was dissolved in dichloromethane
  5. addition3 mL of 1 N HCl in diethyl ether and 50 mL of diethyl ether were added
  6. customto form a precipitate that
  7. filtrationwas collected by vacuum filtration
  8. customAfter drying

Sources & evidence

ORD record
ord-b083c6100e4b4eea844e4ac00200b6b7
Source dataset
uspto-grants-2006_07
Patent number
US07071231B2

Reaction notes

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