Triethylamine → HCID 19707506, compound

HRID 726748

Reaction equation

HRID 726748 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=2[O:16][CH3:17])[CH2:10][CH2:11][NH2:12])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:25][O:26][CH2:27][C:28](Cl)=[O:29]>O1CCCC1>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:10][CH2:11][NH:12][C:28](=[O:29])[CH2:27][O:26][CH3:25])[CH:13]=[CH:14][C:15]=2[O:16][CH3:17])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 112763943-Cyclopentyloxy-4-methoxyphenethylamine

Product 1

HCID 19707506HCID 19707506, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-cyclopentyloxy-4-methoxyphenethylamine (0.2 g, 0.85 mmol) in tetrahydrofuran (6 mL) was cooled to 0° C. and was treated with triethylamine (0.13 mL, 0.92 mmol) and methoxyacetyl chloride (0.078 mL, 0.85 mmol). The reaction was stirred under an argon atmosphere for 0.25 h, then was partitioned between methylene chloride and water. The extract was dried (potassium carbonate) and evaporated. Purification by flash chromatography, eluting with 5% methanol/chloroform, provided an oil; additional 0.1 g of impure product also obtained).

Workup

  1. customwas partitioned between methylene chloride and water
  2. dry with materialThe extract was dried (potassium carbonate)
  3. customevaporated
  4. customPurification by flash chromatography
  5. washeluting with 5% methanol/chloroform
  6. customprovided an oil

Sources & evidence

ORD record
ord-91f4cebc236d47f8883b51e796df83af
Source dataset
uspto-grants-1998_01
Patent number
US05710180

Linked notes

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