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

HRID 611132Notes

Reaction equation

HRID 611132 reaction equation
[CH2:1]([C:8]1[CH:24]=[CH:23][C:11]([C:12]([N:14]2[CH2:19][CH2:18][C:17]3[CH:20]=[CH:21][O:22][C:16]=3[CH2:15]2)=[O:13])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:25][NH:26][CH3:27].[CH2:28]=O>C(O)(=O)C>[CH3:25][N:26]([CH2:28][C:21]1[O:22][C:16]2[CH2:15][N:14]([C:12](=[O:13])[C:11]3[CH:23]=[CH:24][C:8]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH:9][CH:10]=3)[CH2:19][CH2:18][C:17]=2[CH:20]=1)[CH3:27]

Participants

5

Reactant 3

HCID 674Dimethylamine2×HCID 712Formaldehyde2×HCID 195999886-(4-Heptylbenzoyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

Product 1

HCID 19600030N,N-dimethyl-[6-(4-heptylbenzoyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridin-2-ylmethyl]amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 0.260 g (0.799 mmol) of 6-(4-heptylbenzoyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine in 20 ml of acetic acid, 0.108 ml (1.20 mmol) of 50% aqueous dimethylamine and 0.097 ml (1.20 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 60 minutes. Additionally, 0.072 ml (0.799 mmol) of 50% aqueous dimethylamine and 0.064 ml (0.799 mmol) of 37% aqueous formaldehyde were added, followed by stirring for 30 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with 5% aqueous solution of 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 to 25/1) to yield the desired product.

Workup

  1. stirringby stirring for 30 minutes
  2. distillationAfter the solvent was distilled off under reduced pressure
  3. extractionextracted with dichloromethane 2 times
  4. washThe combined organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting crude product was purified by silica gel column chromatography (chloroform to chloroform/methanol=50/1 to 25/1)

Sources & evidence

ORD record
ord-64fcc190066646e3982273be758a6a8e
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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