3-(4-Hydroxyphenyl)propionic acid → N-benzyl-N-hexyl-3-(4-hydroxyphenyl)propanamide

HRID 899865

Reaction equation

HRID 899865 reaction equation
[CH2:1]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([OH:26])=O)=[CH:18][CH:17]=1.C1C=CC2N(O)N=NC=2C=1.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>[CH2:8]([N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:24](=[O:26])[CH2:23][CH2:22][C:19]1[CH:18]=[CH:17][C:16]([OH:15])=[CH:21][CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 5

HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 485395Benzenemethanamine, N-hexyl-HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 69120664N-benzyl-N-hexyl-3-(4-hydroxyphenyl)propanamideYield 71.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-hexylbenzylamine (0.6 g, 3.136 mmol) and 3-(4-hydroxyphenyl)propionic acid (0.52 g 3.136 mmol) were mixed in DMF (10 ml) and the mixture was cooled. HOBT (0.424 g, 3.136 mmol) and the TBTU (1 g, 3.136 mmol) reagent were added followed by DIPEA (1.216 g, 9.409 mmol). The mixture was stirred at room temperature overnight and then evaporated. The resulting mixture was partitioned between ethyl acetate and sodium hydrogencarbonate aqueous solution (sat.). The aqueous portion was extracted with ethyl acetate and the combined organic extracts dried with magnesium sulphate and then evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 5 g/25 ml) using ethyl acetate/heptane (10:90, then 25:75) as eluant gave 760 mg the desired product, yield 71%.

Workup

  1. temperaturethe mixture was cooled
  2. customevaporated
  3. customThe resulting mixture was partitioned between ethyl acetate and sodium hydrogencarbonate aqueous solution (sat.)
  4. extractionThe aqueous portion was extracted with ethyl acetate
  5. dry with materialthe combined organic extracts dried with magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-f47c460ec7e348ac82cab9f315f3f4cf
Source dataset
uspto-grants-2008_04
Patent number
US07355069B2

Linked notes

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