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

HRID 611271
Notes
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Reaction equation

HRID 611271 reaction equation
[CH3:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[C:4]([C:6]1[CH:22]=[CH:21][C:9]([C:10]([N:12]2[CH2:17][CH2:16][C:15]3[CH:18]=[CH:19][O:20][C:14]=3[CH2:13]2)=[O:11])=[CH:8][CH:7]=1)=[O:5].[CH3:27][NH:28][CH3:29].[CH2:30]=O>C(O)(=O)C>[CH3:27][N:28]([CH2:30][C:19]1[O:20][C:14]2[CH2:13][N:12]([C:10](=[O:11])[C:9]3[CH:21]=[CH:22][C:6]([C:4](=[O:5])[C:3]4[CH:23]=[CH:24][CH:25]=[CH:26][C:2]=4[CH3:1])=[CH:7][CH:8]=3)[CH2:17][CH2:16][C:15]=2[CH:18]=1)[CH3:29]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 196000596-[4-(2-Methylbenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

Product 1

HCID 19599918N,N-dimethyl-[6-[4-(2-methylbenzoyl)benzoyl]-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 (0.724 mmol) of 6-[4-(2-methylbenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridine in 10 ml of acetic acid, 0.098 ml (1.09 mmol) of 50% aqueous dimethylamine and 0.088 ml (1.09 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 120 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 magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate/methanol=5/1) 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 magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate/methanol=5/1)

Sources & evidence

ORD record
ord-17cf343580ad4c549c03b301eadace28
Source dataset
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05998433

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes