Dimethylformamide → HCID 69901123, compound

HRID 1884248Notes

Reaction equation

HRID 1884248 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14](=[O:26])[CH2:15][C:16]2[CH:25]=[CH:24][C:23]3[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=3[CH:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(O[CH:32](N(C)C)[N:33]([CH3:35])[CH3:34])(C)(C)C.CN(C)C=O>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14](=[O:26])[C:15]([C:16]2[CH:25]=[CH:24][C:23]3[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=3[CH:17]=2)=[CH:32][N:33]([CH3:35])[CH3:34])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 17471905HCID 17471905, compound

Product 1

HCID 69901123HCID 69901123, compoundYield 107.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

2.65 g (7.50 mmol) of N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(5,6,7,8-tetrahydronaphthalen-2-yl)acetamide, 3.92 g (22.5 mmol) of t-butoxybis (dimethylamino)methane and 30 ml of N,N-dimethylformamide were mixed and stirred at 90° C. for 3 hours and then at 110° C. for 3 hours. Water was added to the reaction mixture, which was followed by extracted with ethyl acetate, washed with saturated brine twice, dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure to give 3.30 g of crude N-[2-(3,4-dimethoxyphenyl)ethyl]-3-dimethylamino-2-(5,6,7,8-tetrahydronaphthalen-2-yl)acrylamide.

Workup

  1. waitat 110° C. for 3 hours
  2. extractionby extracted with ethyl acetate
  3. washwashed with saturated brine twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-fe0ff08c79464287a2141184fcee8876
Source dataset
uspto-grants-2004_07
Patent number
US06762321B2

Reaction notes

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