Tyramine → HCID 19363452, compound

HRID 850480Notes

Reaction equation

HRID 850480 reaction equation
[CH2:1]([O:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:11]([OH:13])=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].O.ON1C2C=CC=CC=2N=N1.[OH:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42][CH2:43][NH2:44])=[CH:38][CH:37]=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:11]([NH:44][CH2:43][CH2:42][C:39]1[CH:40]=[CH:41][C:36]([OH:35])=[CH:37][CH:38]=1)=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 5610TyramineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 14749432HCID 14749432, compound

Product 1

HCID 19363452HCID 19363452, compoundYield 104.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3,4-Dihexyloxybenzoic acid (161 mg, 0.5 mmol) and 1-hydroxy-benzotriazole hydrate (45.9 mg, 0.3 mmol, 0.6 eq) were dissolved in DMF (5 ml), and to this solution were successively added 2-(4-hydroxyphenyl)ethylamine (82 mg, 0.6 mmol, 1.2 eq) and WSC hydrochloride (114 mg, 0.6 mmol, 1.2 eq) at room temperature. The mixture was stirred at room temperature for 15 hours. This reaction mixture was poured into ethyl acetate (75 ml), washed with water (5 ml×3) and saturated brine (15 ml). The organic layerwas dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (chloroform/methanol=50/1) to give 3,4-dihexyloxy-N-[2-(4-hydroxyphenyl)ethyl]benzamide (230 mg). The obtained solid was recrystallized from ethyl acetate-hexane to give 3,4-dihexyloxy-N-[2-(4-hydroxyphenyl)ethyl]benzamide (194 mg, 88%) as colorless crystals.

Workup

  1. customat room temperature
  2. washwashed with water (5 ml×3) and saturated brine (15 ml)
  3. dry with materialThe organic layerwas dried over anhydrous sodium sulfate
  4. filtrationThe drying agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by column chromatography on silica gel (chloroform/methanol=50/1)

Sources & evidence

ORD record
ord-feb77de93dce42ea88c57e5d5ce690eb
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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