Triethylamine → 2-Butyl-benzofuran-3-carboxylic acid benzyl-(6-hydroxy-naphthalen-2-ylmethyl)-amide

HRID 1357295Notes

Reaction equation

HRID 1357295 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=2[C:9]=1[C:10](Cl)=[O:11])[CH2:2][CH2:3][CH3:4].[CH2:17]([NH:24][CH2:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[CH:32]=[C:31]([OH:36])[CH:30]=[CH:29]2)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[CH2:17]([N:24]([CH2:25][C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[C:31]([OH:36])[CH:32]=2)[CH:27]=1)[C:10]([C:9]1[C:8]2[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=2[O:6][C:5]=1[CH2:1][CH2:2][CH2:3][CH3:4])=[O:11])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 185052776-(Benzylamino-methyl)-naphthalen-2-olHCID 185053462-Butyl-benzofuran-3-carbonyl chloride

Product 1

HCID 691391852-Butyl-benzofuran-3-carboxylic acid benzyl-(6-hydroxy-naphthalen-2-ylmethyl)-amideYield 65.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2-Butyl-benzofuran-3-carbonyl-chloride (3 mmol), prepared in step 2 of Example 3, in 25 mL of anhydrous THF was added under nitrogen dropwise over 1 h to a solution of 6-(benzylamino-methyl)-naphthalen-2-ol (0.71 g, 2.7 mmol), prepared in the previous step, and triethylamine (0.376 mL, 2.7 mmol) in 75 mL of anhydrous THF at room temperature. After the addition the reaction was stirred at room temperature for 20 h (overnight). The solid present was removed by filtration and the filtrate concentrated under reduced pressure to give a brown oil. The oil was dissolved in ethyl acetate and extracted with 1N HCl. The organic layer was dried (MgSO4) and the solvent removed under reduced pressure. Chromatography of the crude oil on 200 g of silica gel (230-400 mesh) using 0%-5% ethyl acetate in methylene chloride as the eluent gave 2-butyl-benzofuran-3-carboxylic acid benzyl-(6-hydroxy-naphthalen-2-ylmethyl)-amide (0.8164 g, 65%) as a light yellow solid, mp 160-164° C.

Workup

  1. additionAfter the addition the reaction
  2. customThe solid present was removed by filtration
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customto give a brown oil
  5. extractionextracted with 1N HCl
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-89dbd9c1034b403ebb93356ea9eeb75c
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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