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Potassium Carbonate → N-[3-hydroxy-2-(7-methoxy-1-naphthyl)propyl]propionamide

HRID 2374727
Notes
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Reaction equation

HRID 2374727 reaction equation
Cl.[NH2:2][CH2:3][CH:4]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[CH:10]=[CH:9][CH:8]=1)[CH2:5][OH:6].C(=O)([O-])[O-].[K+].[K+].[Cl-].[CH2:26]([OH:29])[CH2:27][CH3:28]>O.C(OCC)(=O)C>[OH:6][CH2:5][CH:4]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[CH:10]=[CH:9][CH:8]=1)[CH2:3][NH:2][C:26](=[O:29])[CH2:27][CH3:28]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 20289515Propanol chlorideHCID 685970113-Amino-2-(7-methoxy-1-naphthyl)-1-propanol hydrochloride

Product 1

HCID 23642306N-[3-hydroxy-2-(7-methoxy-1-naphthyl)propyl]propionamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
0 °C

Procedure

The compound obtained in Step B (3.73 mmol) is dissolved in 100 ml of a mixture of water and ethyl acetate (50/50). Potassium carbonate (11.2 mmol) is added and the reaction mixture is cooled to 0° C. Using an ice bath. Propanol chloride (4.6 mmol) is added dropwise and the mixture is stirred for 15 minutes in the cold state. When the reaction is complete, the organic phase is washed with hydrochloric acid solution (1M), washed with water, dried and evaporated under reduced pressure. The solution obtained is recrystallized from acetonitrile to yield the title product in the form of a white solid.

Workup

  1. washthe organic phase is washed with hydrochloric acid solution (1M)
  2. washwashed with water
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe solution obtained
  6. customis recrystallized from acetonitrile

Sources & evidence

ORD record
ord-8aab6b6d8ade4254a73129bf8d4f58e8
Source dataset
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07462741B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes