Homovanillic Acid → N-Benzyl-N-hexyl-2-(4-hydroxy-3-methoxyphenyl)acetamide

HRID 2111991

Reaction equation

HRID 2111991 reaction equation
[C:1]([OH:13])(=O)[CH2:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[CH2:14]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:21]([N:20]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:1](=[O:13])[CH2:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 1738Homovanillic AcidHCID 81531DiisopropylethylamineHCID 485395Benzenemethanamine, N-hexyl-HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 68872097N-Benzyl-N-hexyl-2-(4-hydroxy-3-methoxyphenyl)acetamideYield 74.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Homovanillic acid (182 mg, 0.999 mmol) dissolved in DMF (3 ml) was cooled in an ice-bath. N-Hexylbenzylamine (201 mg, 1.049 mmol) was added and then TBTU (337 mg, 1.049 mmol) followed by DIPEA (407 mg, 3.147 mmol). The mixture was stirred at room temperature overnight and evaporated. Sodium hydrogencarbonate aqueous solution (sat.) was added into the residue. The mixture was then extracted with ethyl acetate (×2). The extracts were combined and washed with water and brine and dried (magnesium sulphate) and evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 5 g/15 ml) using DCM and then MeOH/DCM (1:99) as eluant gave 264 mg the desired product, yield 74%.

Workup

  1. temperaturewas cooled in an ice-bath
  2. customevaporated
  3. additionSodium hydrogencarbonate aqueous solution (sat.) was added into the residue
  4. extractionThe mixture was then extracted with ethyl acetate (×2)
  5. washwashed with water and brine
  6. dry with materialdried (magnesium sulphate)
  7. customevaporated

Sources & evidence

ORD record
ord-13acd9a2856e486e95d3b6683b2e8262
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Linked notes

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