Hydrochloric Acid → HCID 18766408, compound

HRID 480697Notes

Reaction equation

HRID 480697 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[CH2:13]([NH2:16])[CH2:14][CH3:15].Cl>O1CCCC1.C(Cl)Cl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([NH:16][CH2:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7852PropylamineHCID 103943-(4-Hydroxyphenyl)propionic acid

Product 1

HCID 18766408HCID 18766408, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-(4-Hydroxyphenyl)propionic acid (12.0 g, 72.0 mmol) was dissolved in tetrahydrofuran (20 mL). n-Propylamine (5.1 g, 86.4 mmol) was added dropwise at room temperature. Subsequently, under ice-cooling, solution (20 mL) of WSCI-hydrochloric acid salt (16.5 g, 86.4 mmol) in methylene chloride was slowly added thereto, and the resultant mixture was stirred overnight. Diluted hydrochloric acid was added dropwise under ice-cooling, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, followed by drying over sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (chloroform/methanol=50/1), whereby the target compound was obtained (9.7 g, 65%).

Workup

  1. temperatureSubsequently, under ice-cooling
  2. temperaturecooling
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialby drying over sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (chloroform/methanol=50/1), whereby the target compound
  6. customwas obtained (9.7 g, 65%)

Sources & evidence

ORD record
ord-33d05d4af43b41cd9b316589b34dcdd6
Source dataset
uspto-grants-2003_11
Patent number
US06653334B1

Reaction notes

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