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Formaldehyde → 6-[4-(1-Phenylethenyl)benzoyl]-2-(1-pyrrolidinylmethyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

HRID 611371
Notes
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Reaction equation

HRID 611371 reaction equation
[C:1]1([C:7]([C:9]2[CH:25]=[CH:24][C:12]([C:13]([N:15]3[CH2:20][CH2:19][C:18]4[CH:21]=[CH:22][O:23][C:17]=4[CH2:16]3)=[O:14])=[CH:11][CH:10]=2)=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1.[CH2:31]=O>C(O)(=O)C>[C:1]1([C:7]([C:9]2[CH:25]=[CH:24][C:12]([C:13]([N:15]3[CH2:20][CH2:19][C:18]4[CH:21]=[C:22]([CH2:31][N:26]5[CH2:30][CH2:29][CH2:28][CH2:27]5)[O:23][C:17]=4[CH2:16]3)=[O:14])=[CH:11][CH:10]=2)=[CH2:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 31268PyrrolidineHCID 196001706-[4-(1-Phenylethenyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

Product 1

HCID 195999626-[4-(1-Phenylethenyl)benzoyl]-2-(1-pyrrolidinylmethyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 0.724 g (2.198 mmol) of the above 6-[4-(1-phenylethenyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridine in 10 ml of acetic acid, 0.28 ml (3.30 mmol) of pyrrolidine and 0.27 g (3.30 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 aqueous sodium hydroxide and extracted with ethyl acetate 3 times. The combined organic layer was 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 to ethyl acetate/methanol=4/1) to yield the desired product.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. extractionextracted with ethyl acetate 3 times
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=4/1)

Sources & evidence

ORD record
ord-de2dcade8bff474fae37a56fdceaf80b
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