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

HRID 611107Notes

Reaction equation

HRID 611107 reaction equation
[C:1]([C:9]1[CH:25]=[CH:24][C:12]([C:13]([N:15]2[CH2:20][CH2:19][C:18]3[O:21][CH:22]=[CH:23][C:17]=3[CH2:16]2)=[O:14])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][NH:27][CH3:28].[CH2:29]=O>C(O)(=O)C>[CH3:26][N:27]([CH2:29][C:22]1[O:21][C:18]2[CH2:19][CH2:20][N:15]([C:13](=[O:14])[C:12]3[CH:11]=[CH:10][C:9]([C:1](=[O:8])[C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:25][CH:24]=3)[CH2:16][C:17]=2[CH:23]=1)[CH3:28]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 195999475-(4-Benzoylbenzoyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridine

Product 1

HCID 19600014N,N-dimethyl-[5-(4-benzoylbenzoyl)-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 0.230 g (0.694 mmol) of 5-(4-benzoylbenzoyl)-4,5,6,7-tetrahydrofuro[3,2-c]pyridine in 20 ml of acetic acid, 0.094 ml (1.04 mmol) of 50% aqueous dimethylamine and 0.085 ml (1.04 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 1 hour. 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 to chloroform/methanol=50/1); the resulting solid was washed with hexane 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 to chloroform/methanol=50/1)
  7. washthe resulting solid was washed with hexane

Sources & evidence

ORD record
ord-0e545bda568d4d47bc9aed685acf3dc8
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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