Triethylamine → N-(8-methoxytetralin-2-yl)-N-propyl-2-(2-thienyl)acetamide

HRID 2362596Notes

Reaction equation

HRID 2362596 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][CH:10]([NH:13][CH2:14][CH2:15][CH3:16])[CH2:9][CH2:8]2.CCN(CC)CC.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[CH2:29][C:30](Cl)=[O:31]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][CH:10]([N:13]([CH2:14][CH2:15][CH3:16])[C:30](=[O:31])[CH2:29][C:25]1[S:24][CH:28]=[CH:27][CH:26]=1)[CH2:9][CH2:8]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1623622-Thiopheneacetyl chloride2×HCID 127414178-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine

Product 1

HCID 67251740N-(8-methoxytetralin-2-yl)-N-propyl-2-(2-thienyl)acetamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 60 mg (0.27 mmol) of the free base of N-(8-methoxytetralin-2-yl)-N-propylamine (A2-1) and 0.11 mL Et3N (0.79 mmol) in 5 mL dry CHCl3 was cooled in an ice bath. After adding 0.05 ml (0.41 mmol) 2-thienylacetic acid chloride (A3-1: W=Cl, Cy=2-thienyl) to the mixture the ice bath was removed and the reaction was stirred for 2 hrs at room temperature. In a second step further 0.05 mL (0.41 mmol) of 2-thienylacetic acid chloride (A3-1) were added and the reaction stirred for 20 hrs. The mixture was washed with a saturated solution of aqueous NaHCO3 for several times and finally extracted with CH2Cl2. The organic layers were dried over MgSO4 and the solvent was evaporated in vacuo. Flash chromatography of the residue on silica gel with a mixture of hexane/ethyl acetate 40/1 gave the product N-(8-methoxytetralin-2-yl)-N-propyl-2-(2-thienyl)acetamide.

Workup

  1. customwas removed
  2. stirringthe reaction stirred for 20 hrs
  3. washThe mixture was washed with a saturated solution of aqueous NaHCO3 for several times
  4. extractionfinally extracted with CH2Cl2
  5. dry with materialThe organic layers were dried over MgSO4
  6. customthe solvent was evaporated in vacuo
  7. additionFlash chromatography of the residue on silica gel with a mixture of hexane/ethyl acetate 40/1

Sources & evidence

ORD record
ord-dd6b7dc2a6324902a2456cb5172ebd80
Source dataset
uspto-grants-2014_04
Patent number
US08691839B2

Reaction notes

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