N-Methylpiperidine → HCID 53834253, compound

HRID 1900207Notes

Reaction equation

HRID 1900207 reaction equation
CN1CCCCC1.Cl.[C:9]([C:11]1[CH:28]=[CH:27][C:14]([O:15][CH:16]([CH3:26])[CH2:17][NH:18][C:19](=[O:25])[C@H:20]([CH:22]([CH3:24])[CH3:23])[NH2:21])=[CH:13][CH:12]=1)#[N:10].Cl[C:30]([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:31]>C(Cl)Cl>[C:9]([C:11]1[CH:12]=[CH:13][C:14]([O:15][CH:16]([CH3:26])[CH2:17][NH:18][C:19](=[O:25])[C@H:20]([CH:22]([CH3:24])[CH3:23])[NH:21][C:30]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:31])=[CH:27][CH:28]=1)#[N:10]

Participants

5

Reactant 3

HCID 12291N-MethylpiperidineHCID 15891Phenyl chloroformateHCID 22866850HCID 22866850, compound

Product 1

HCID 53834253HCID 53834253, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.16 g of N-methylpiperidine was added to a suspension containing 0.25 g of N1 -[2-(4-cyanophenoxy)propyl]-L-valinamide hydrochloride suspended in 20 ml of methylene chloride, at -20° C. After the mixture was stirred for 10 minutes at the same temperature, 0.13 g of phenyl chloroformate was added drop by drop to the mixture, and then the reaction mixture was allowed to sit and warm naturally to room temperature while being stirred, and was stirred for 3 hours at room temperature. After the methylene chloride was removed under reduced pressure, the residue was purified by column chromatography on silica gel, thus obtaining 0.2 g of the desired product in the form of a white glutinous substance (yield: 63%).

Workup

  1. additionwas added drop by drop to the mixture
  2. stirringwas stirred for 3 hours at room temperature
  3. customAfter the methylene chloride was removed under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-bf9d41e0f74a453aa54bf2ac4e1bbd6b
Source dataset
uspto-grants-1996_11
Patent number
US05574064

Reaction notes

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