Dimethylamine → N,N-Dimethyl-(5-[4-(4-methoxybenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[3,2-c]pyridin-2-ylmethyl]amine

HRID 611262Notes

Reaction equation

HRID 611262 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([C:7]([C:9]2[CH:25]=[CH:24][C:12]([C:13]([N:15]3[CH2:20][CH2:19][C:18]4[O:21][CH:22]=[CH:23][C:17]=4[CH2:16]3)=[O:14])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.[CH3:28][NH:29][CH3:30].[CH2:31]=O>C(O)(=O)C>[CH3:28][N:29]([CH2:31][C:22]1[O:21][C:18]2[CH2:19][CH2:20][N:15]([C:13](=[O:14])[C:12]3[CH:24]=[CH:25][C:9]([C:7](=[O:8])[C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:27][CH:26]=4)=[CH:10][CH:11]=3)[CH2:16][C:17]=2[CH:23]=1)[CH3:30]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 196002365-[4-(4-Methoxybenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[3,2-c]pyridine

Product 1

HCID 19600124N,N-Dimethyl-(5-[4-(4-methoxybenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[3,2-c]pyridin-2-ylmethyl]amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 0.350 g (0.968 mmol) of 5-[4-(4-methoxybenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[3,2-c]pyridine in 10 ml of acetic acid, 0.131 ml (1.45 mmol) of 50% aqueous dimethylamine and 0.118 ml (1.45 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 90 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with 5% aqueous sodium hydrogen carbonate and extracted with dichloromethane 2 times. The combined organic layer was washed with water and dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (chloroform/methanol=50/1 to 25/1). This was washed with diethyl ether to yield the desired product.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. extractionextracted with dichloromethane 2 times
  3. washThe combined organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting crude product was purified by silica gel column chromatography (chloroform/methanol=50/1 to 25/1)
  7. washThis was washed with diethyl ether

Sources & evidence

ORD record
ord-5e3d11b9c27149d7b5855765c307da43
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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