Triethylamine → 2,2-dimethyl-N-(6,7,8,9-tetrahydro-dibenzofuran-2-yl)-propionamide
Reaction equation
C(N(CC)CC)C.[CH:8]1[C:16]2[C:15]3[CH2:17][CH2:18][CH2:19][CH2:20][C:14]=3[O:13][C:12]=2[CH:11]=[CH:10][C:9]=1[NH2:21].[CH3:22][C:23]([CH3:28])([CH3:27])[C:24](Cl)=[O:25]>>[CH3:22][C:23]([CH3:28])([CH3:27])[C:24]([NH:21][C:9]1[CH:10]=[CH:11][C:12]2[O:13][C:14]3[CH2:20][CH2:19][CH2:18][CH2:17][C:15]=3[C:16]=2[CH:8]=1)=[O:25]Participants
Conditions
- Temperature
- 0 °C
Procedure
Triethylamine (2.0 mL, 14 mmol) was added to a cooled (0° C.) solution of 6,7,8,9-tetrahydro-dibenzofuran-2-ylamine (0.86 g, 4.6 mmol). The reaction mixture was stirred for 10 minutes at 0° C. and then trimethylacetyl chloride (0.60 mL, 4.8 mmol) was added. The ice bath was removed and the reaction mixture was stirred for 30 min and then concentrated. The crude material was dissolved in chloroform and washed with 10% aqueous ammonium hydroxide, water, and brine, dried (Na2SO4) and concentrated. The crude material was recrystallized from acetonitrile to provide 2,2-dimethyl-N-(6,7,8,9-tetrahydro-dibenzofuran-2-yl)-propionamide (0.80 g). Mp 210-211° C.; Anal. Calcd. for C17H21NO2: C, 75.25; H, 7.80; N, 5.16; Found: C, 75.33; H, 7.64; N, 5.07.
Workup
- customThe ice bath was removed
- stirringthe reaction mixture was stirred for 30 min
- concentrationconcentrated
- dissolutionThe crude material was dissolved in chloroform
- washwashed with 10% aqueous ammonium hydroxide, water, and brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customThe crude material was recrystallized from acetonitrile
Sources & evidence
- ORD record
- ord-179eee6e05734d1e85060be72eed9840
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07601856B2
Reaction notes
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