2,4,5-Trimethoxybenzaldehyde → N-cyclohexyl-N-cyclopentyl-4-[hydroxy(2,4,5-trimethoxyphenyl)methyl]benzamide

HRID 1588929Notes

Reaction equation

HRID 1588929 reaction equation
Br[C:2]1[CH:21]=[CH:20][C:5]([C:6]([N:8]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:7])=[CH:4][CH:3]=1.C([Li])(C)(C)C.[CH3:27][O:28][C:29]1[CH:36]=[C:35]([O:37][CH3:38])[C:34]([O:39][CH3:40])=[CH:33][C:30]=1[CH:31]=[O:32]>C1COCC1>[CH:14]1([N:8]([CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[C:6](=[O:7])[C:5]2[CH:20]=[CH:21][C:2]([CH:31]([OH:32])[C:30]3[CH:33]=[C:34]([O:39][CH3:40])[C:35]([O:37][CH3:38])=[CH:36][C:29]=3[O:28][CH3:27])=[CH:3][CH:4]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 205252,4,5-TrimethoxybenzaldehydeHCID 197548884-bromo-N-cyclohexyl-N-cyclopentylbenzamideHCID 178418306HCID 178418306, compound

Product 1

HCID 19754870N-cyclohexyl-N-cyclopentyl-4-[hydroxy(2,4,5-trimethoxyphenyl)methyl]benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cold (-70° C.), stirred solution of 4-bromo-N-cyclohexyl-N-cyclopentylbenzamide (1.5 g, 4.3 mmol) in THF (20 ml) was added slowly a solution of tertbutyllithium (5 ml of 1.7 M solution in pentane) under an Argon atmosphere. The reaction was stirred at -70° to -75° for 20 min. and a solution of 2,4,5-trimethoxybenzaldehyde (843 mg, 4.3 mmol) in THF (10 ml) was added dropwise over 30 min. The reaction was stirred at -70° to -75° for 30 min. and at room temperature for 1 hr. The reaction was quenched by the addition of water and the aqueous layer extracted three times with ethyl acetate. The combined organic layers were washed with water and dried (Na2SO4). The drying agent was filtered and the filtrate concentrated in vacuo to give the crude product. Purification was effected by chromatography on silica gel using mixtures of ethyl acetate and hexane. The product was isolated as a glass.

Workup

  1. stirringThe reaction was stirred at -70° to -75° for 30 min. and at room temperature for 1 hr
  2. customThe reaction was quenched by the addition of water
  3. extractionthe aqueous layer extracted three times with ethyl acetate
  4. washThe combined organic layers were washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationThe drying agent was filtered
  7. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-5d0d7e9bff4f43be89c0f6c5c292cc33
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

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