Tetrahydrofuran → N-Propionylserotonin

HRID 1636602

Reaction equation

HRID 1636602 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][C:4]2[C:8]([CH2:11][CH2:12][NH2:13])=[CH:9][NH:10][C:3]=2[CH:2]=1.Cl.[O:15]1C[CH2:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[Na+].[Na+].C(OC(=O)CC)(=O)CC>O>[OH:7][C:6]1[CH:5]=[C:4]2[C:3](=[CH:2][CH:1]=1)[NH:10][CH:9]=[C:8]2[CH2:11][CH2:12][NH:13][C:16](=[O:15])[CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 31263Propionic anhydrideHCID 160436Serotonin Hydrochloride

Product 1

HCID 594440N-PropionylserotoninYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of serotonin hydrochloride (10 g, 47.5 mmol.) in water (50 mL) were added, under argon atmosphere, tetrahydrofuran (20 mL) and a solution of sodium carbonate (5.3 g) in water (20 mL). The mixture was cooled to 0° C., to which was added propionic anhydride (6.2 g, 49.9 mmol.). The mixture was stirred for 2 hours at room temperature. The reaction mixture was subjected to extraction with ethyl acetate. The extract solution was washed with 1N HCl, a saturated aqueous solution of sodium hydrogencarbonate and water, which was dried and then concentrated to afford the title compound (yield 10.0 g, 98.0%) as an oily product. This compound was used, without refining further, for the subsequent reaction.

Workup

  1. extractionThe reaction mixture was subjected to extraction with ethyl acetate
  2. washThe extract solution was washed with 1N HCl
  3. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and water, which was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-abaf09a40ccd4d5f937b64db7123252f
Source dataset
uspto-grants-2000_03
Patent number
US06034239

Linked notes

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