HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Methyl iodide → Allyl 1-(4-allyloxy-3-methoxycinnamoyl)-4-methylpiperidine-4-carboxylate

HRID 2225516
Notes
Print preview

Reaction equation

HRID 2225516 reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[Na+].[CH3:11]I.[CH2:13]([O:16][C:17]1[CH:38]=[CH:37][C:20]([CH:21]=[CH:22][C:23]([N:25]2[CH2:30][CH2:29][CH:28]([C:31]([O:33][CH2:34][CH:35]=[CH2:36])=[O:32])[CH2:27][CH2:26]2)=[O:24])=[CH:19][C:18]=1[O:39][CH3:40])[CH:14]=[CH2:15].[Cl-].[NH4+]>C1COCC1>[CH2:13]([O:16][C:17]1[CH:38]=[CH:37][C:20]([CH:21]=[CH:22][C:23]([N:25]2[CH2:26][CH2:27][C:28]([CH3:11])([C:31]([O:33][CH2:34][CH:35]=[CH2:36])=[O:32])[CH2:29][CH2:30]2)=[O:24])=[CH:19][C:18]=1[O:39][CH3:40])[CH:14]=[CH2:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 53802979Allyl 1-(4-allyloxy-3-methoxycinnamoyl)-piperidine-4-carboxylate

Product 1

HCID 53899198Allyl 1-(4-allyloxy-3-methoxycinnamoyl)-4-methylpiperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

50 ml of sodium hexamethyldisilazide (1M solution in THF) and 5.3 ml of methyl iodide were added to a solution of 7.8 g of allyl 1-(4-allyloxy-3-methoxycinnamoyl)-piperidine-4-carboxylate (Example 66) in 200 ml of THF. The solution was reacted for 18 hours at room temperature. After reaction, 200 ml of an aqueous ammonium chloride solution was added to the reaction solution. The solution was extracted three times with 100 ml of ethyl acetate. The organic layer obtained was washed twice with an aqueous sodium chloride solution and dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo. The oily substance obtained was subjected to column chromatography using 100 g of silica gel. From the fraction eluted with hexane and ethyl acetate=3:2, the solvent was removed in vacuo, yielding 1.1 g of allyl 1-(4-allyloxy-3-methoxycinnamoyl)-4-methylpiperidine-4-carboxylate (a compound of the present invention) as a pale yellow oil, which had the following physiochemical properties:

Workup

  1. customThe solution was reacted for 18 hours at room temperature
  2. additionwas added to the reaction solution
  3. extractionThe solution was extracted three times with 100 ml of ethyl acetate
  4. customThe organic layer obtained
  5. washwas washed twice with an aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThereafter, the solvent was removed in vacuo
  8. customThe oily substance obtained
  9. washFrom the fraction eluted with hexane and ethyl acetate=3:2
  10. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4fe99b66cfdd47f4b11020fdfbb8b832
Source dataset
uspto-grants-1994_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05344845

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes