Formaldehyde → HCID 70204360, compound

HRID 611560Notes

Reaction equation

HRID 611560 reaction equation
[ClH:1].Cl.[NH:3]1[CH2:7][CH2:6][CH2:5][C@H:4]1[C:8]1[O:16][C:15]2[C:10](=[N:11][C:12]([CH3:17])=[CH:13][CH:14]=2)[CH:9]=1.[CH2:18]=O>C(O)=O.Cl>[ClH:1].[ClH:1].[CH3:18][N:3]1[CH2:7][CH2:6][CH2:5][C@H:4]1[C:8]1[O:16][C:15]2[C:10](=[N:11][C:12]([CH3:17])=[CH:13][CH:14]=2)[CH:9]=1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 70207181HCID 70207181, compound

Product 1

HCID 70204360HCID 70204360, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A 315 mg (1.04 mmol) sample of 2-(2-(S)-pyrrolidinyl)-5-methylfuro[3,2-b]pyridine dihydrochloride, from Example 5b above, was dissolved in 5 mL of 88% formic acid and 10 mL of 37% aqueous formaldehyde and heated at reflux for 0.5 hours. The reaction mixture was cooled, diluted with 2 N HCl and extracted with ether. The aqueous solution was adjusted to pH 10 with K2CO3 and extracted with CH2Cl2. The CH2Cl2 extract was dried over MgSO4, and the solvent was removed. The residue was chromatographed on silica gel, eluting with 100:0 to 95:5 CHCl3 :EtOH The residue was converted to the salt by treatment with HCl/ether, and the salt was recrystallized from EtOH/EtOAc to give 332 mg of title compound: 1H NMR (DMSO, 300 MHz) δ 2.13-2.23 (m, 2H), 2.35-2.60 (m, 3H), 2.71 (s, 3H), 2.88 (s, 2H), 3.33 (br s, 1H), 3.70 (br s, 1H), 4.88 (m, 1H), 7.54 (d, 1H, J=8.8 Hz), 7.61 (s, 1H), 8.36 (d, 1H, J=8.5 Hz); MS m/z: 217 (M+H)+, 234 (M+NH4)+ ; Anal. Calcd for C13H16N2O.2.0 HCl.1.0 H2O: C, 50.82; H, 6.55; N, 9.12. Found: C, 50.47; H, 6.77; N, 8.92.

Workup

  1. temperatureat reflux for 0.5 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with ether
  4. extractionextracted with CH2Cl2
  5. extractionThe CH2Cl2 extract
  6. dry with materialwas dried over MgSO4
  7. customthe solvent was removed
  8. customThe residue was chromatographed on silica gel
  9. washeluting with 100:0 to 95:5 CHCl3
  10. customthe salt was recrystallized from EtOH/EtOAc

Sources & evidence

ORD record
ord-d07615adb7854a4fa20dfe815988d6f9
Source dataset
uspto-grants-1999_12
Patent number
US06001849

Reaction notes

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