1-Iodopentane → HCID 178447154, compound

HRID 2225609Notes

Reaction equation

HRID 2225609 reaction equation
C(N(C(C)C)CC)(C)C.I[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[CH3:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([NH:23][C:24](=[O:40])[CH:25]=[CH:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]([OH:37])=[O:36])=[C:29]([O:38][CH3:39])[CH:28]=2)[CH2:19][CH2:18]1>C(Cl)Cl>[CH3:16][C@H:17]1[CH2:18][CH2:19][C@H:20]([NH:23][C:24](=[O:40])[CH:25]=[CH:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]([O:37][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:36])=[C:29]([O:38][CH3:39])[CH:28]=2)[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 123351-IodopentaneHCID 81531DiisopropylethylamineHCID 178490558HCID 178490558, compound

Product 1

HCID 178447154HCID 178447154, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

30 ml of diisopropylethylamine and 1.3 ml of 1-iodopentane were added to a solution of 1.84 g of N-(trans-4-methylcyclohexyl)-4-(carboxymethoxy )- 3-methoxycinnamamide (Example 172) in 50 ml of methylene chloride. The solution was stirred for 16 hours, while it was refluxed. After reaction, the reaction solution was washed three times with 200 ml of an aqueous sodium thiosulfate solution and once with an aqueous sodium chloride solution, and was dried over magnesium sulfate. Then, the solvent was removed in vacuo. The product obtained was recrystallized from methylene chloride/ether, yielding 1.56 g of N-(trans-4-methylcyclohexyl)-4-(pentyloxycarbonylmethoxy) -3-methoxycinnamamide (a compound of the present invention) as white crystal, which had the following physiochemical properties:

Workup

  1. temperaturewas refluxed
  2. customAfter reaction
  3. washthe reaction solution was washed three times with 200 ml of an aqueous sodium thiosulfate solution
  4. dry with materialonce with an aqueous sodium chloride solution, and was dried over magnesium sulfate
  5. customThen, the solvent was removed in vacuo
  6. customThe product obtained
  7. customwas recrystallized from methylene chloride/ether

Sources & evidence

ORD record
ord-6235fe02649d418c8b90eab6bc920746
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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