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

HRID 611126Notes

Reaction equation

HRID 611126 reaction equation
[C:1]1([C:7]2[CH:23]=[CH:22][C:10]([C:11]([N:13]3[CH2:18][CH2:17][C:16]4[CH:19]=[CH:20][O:21][C:15]=4[CH2:14]3)=[O:12])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:24][NH:25][CH3:26].[CH2:27]=O>C(O)(=O)C>[CH3:24][N:25]([CH2:27][C:20]1[O:21][C:15]2[CH2:14][N:13]([C:11](=[O:12])[C:10]3[CH:9]=[CH:8][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[CH:23][CH:22]=3)[CH2:18][CH2:17][C:16]=2[CH:19]=1)[CH3:26]

Participants

5

Reactant 3

HCID 674Dimethylamine2×HCID 712Formaldehyde2×HCID 196000916-(4-Phenylbenzoyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

Product 1

HCID 19600119N,N-dimethyl-[6-(4-phenylbenzoyl)-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 0.250 g (0.824 mmol) of 6-(4-phenylbenzoyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine in 20 ml of acetic acid, 0.112 ml (1.24 mmol) of 50% aqueous dimethylamine and 0.101 ml (1.24 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 60 minutes. Additionally, 0.075 ml (0.82 mmol) of 50% aqueous dimethylamine and 0.067 ml (0.82 mmol) of 37% aqueous formaldehyde were added, followed by stirring for 20 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 20 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-07024860433a4981a0f4119d1a89b053
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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