Hydrochloric Acid → N-nonanoyl tyramine

HRID 865803Notes

Reaction equation

HRID 865803 reaction equation
[C:1](Cl)(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[NH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C(N(CC)CC)C.Cl>C1COCC1>[C:1]([NH:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5610TyramineHCID 8471TriethylamineHCID 69819Nonanoyl chloride

Product 1

HCID 15343996N-nonanoyl tyramine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Procedure--Nonanoyl chloride (2.74 m, 14.6 mmol) was added dropwise to a cooled solution of tyramine (1 g, 7.29 mmol) and triethylamine (2.03 ml, 14.6 mmol) in THF (35 ml). The reaction mixture was stirred at room temperature for 48 hours. It was then poured into 10% HCl solution (70 ml) and the mixture was then extracted with ethyl acetate (3×50 ml). The ethyl acetate layer was separated, dried (MgSO4) and concentrated under reduced pressure to give crude N-nonanoyl tyramine. The product was purified by chromatography on a silica gel column eluted with methylene chloride/ethyl acetate (30:1). m.p. 65.9° to 66.7° C. IR (KBr) 3306, 2922, 2851, 1638; 1H NMR δ 6.65-6.98 (d of d, 4 H, aromatic), 7.78 (t, 1 H, NH), 9.15 (s, 1 H, OH). Analysis calculated for C17H27NO2 : C, 73.61; H, 9.81; N, 5.05. Found C, 73.49; H, 9.661; N, 5.31.

Workup

  1. extractionthe mixture was then extracted with ethyl acetate (3×50 ml)
  2. customThe ethyl acetate layer was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-930e1d7c4bc5483c86c7b7f681fa83fb
Source dataset
uspto-grants-1996_10
Patent number
US05567831

Reaction notes

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