Ethyl Acetate → 3-Pyridyl 4-[4-(cyclooctylmethoxy)benzoyl]-1-piperazinecarboxylate

HRID 605811

Reaction equation

HRID 605811 reaction equation
Cl.C(N=C=NC[CH2:8][CH2:9][N:10]([CH3:12])C)C.O[N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22]C=2N=N1.[CH:23]([N:26](C(C)C)CC)(C)C.[CH:32]1([CH2:40][O:41][C:42]2[CH:50]=[CH:49][C:45]([C:46]([OH:48])=O)=[CH:44][CH:43]=2)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.C1(CO)CCCCCCC1.CC[O:63][C:64](C)=[O:65]>CN(C=O)C>[CH:32]1([CH2:40][O:41][C:42]2[CH:43]=[CH:44][C:45]([C:46]([N:10]3[CH2:9][CH2:8][N:26]([C:64]([O:63][C:21]4[CH:22]=[N:14][CH:18]=[CH:19][CH:20]=4)=[O:65])[CH2:23][CH2:12]3)=[O:48])=[CH:49][CH:50]=2)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]1

Participants

8

Reactant 6

HCID 8857Ethyl AcetateHCID 757711-HydroxybenzotriazoleHCID 77196CyclooctanemethanolHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574218414-(Cyclooctylmethoxy)benzoic acid

Product 1

HCID 670670423-Pyridyl 4-[4-(cyclooctylmethoxy)benzoyl]-1-piperazinecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride (150 mg), 1-hydroxybenzotriazole (110 mg) and diisopropylethylamine (0.23 ml) were added to a DMF (5 ml) solution containing the resulting compound (190 mg) and 4-(cyclooctylmethoxy)benzoic acid (176 mg) prepared from cyclooctylmethanol with reference to Reference Example 70, followed by stirring overnight at room temperature. The reaction solution was diluted with EtOAc, the organic layer was washed with aqueous saturated sodium hydrogencarbonate solution, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was recrystallized from EtOAc/hexane to obtain 3-pyridyl 4-[4-(cyclooctylmethoxy)benzoyl]-1-piperazinecarboxylate (240 mg).

Workup

  1. washthe organic layer was washed with aqueous saturated sodium hydrogencarbonate solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-08f67960fcfb40128f1ed3f5e434b715
Source dataset
uspto-grants-2011_03
Patent number
US07915261B2

Linked notes

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