Formaldehyde → HCID 86754944, compound

HRID 611571Notes

Reaction equation

HRID 611571 reaction equation
Cl.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]([Cl:17])=[CH:13][CH:14]=2)[CH:9]=1.C=O.[C:20]([O-])([O-])=O.[K+].[K+]>C(O)=O>[ClH:17].[Cl:17][C:12]1[N:11]=[C:10]2[CH:9]=[C:8]([C@@H:4]3[CH2:5][CH2:6][CH2:7][N:3]3[CH3:20])[O:16][C:15]2=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 86754945HCID 86754945, compound

Product 1

HCID 86754944HCID 86754944, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A 660 mg (1.04 mmol) sample of 2-(2-(S)-pyrrolidinyl)-5-chlorofuro[3,2-b]pyridine dihydrochloride, from Example 11e above, was dissolved in 5 mL of 88% formic acid and 10 mL of 37% aqueous formaldehyde and heated at reflux for 1 hour. The reaction mixture was cooled, poured into saturated K2CO3, and the mixture was extracted with CH2Cl2. The 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 :MeOH. The residue was converted to the salt by treatment with HCl/ether to give 540 mg of title compound: 1H NMR (D2O, 300 MHz) δ 2.28-2.38 (m, 2H), 2.49-2.72 (m, 2H), 2.92 (br s, 3H), 3.41 (m, 1H), 3.80 (m, 1H), 4.84 (m, 1H), 7.50 (d, 1H, J=8.8 Hz), 8.0 (d, 1H, J=8.8 Hz), 8.56 (d, 1H); MS m/z: 237 (M+H)+ ; Anal. Calcd for C12H13N2OCl.1.0 HCl. C, 52.07; H, 5.13; N, 10.12. Found: C, 51.85; H, 5.46; N, 9.78.

Workup

  1. temperatureat reflux for 1 hour
  2. temperatureThe reaction mixture was cooled
  3. extractionthe mixture was extracted with CH2Cl2
  4. dry with materialThe extract was dried over MgSO4
  5. customthe solvent was removed
  6. customThe residue was chromatographed on silica gel
  7. washeluting with 100:0 to 95:5 CHCl3

Sources & evidence

ORD record
ord-722b860c0f364a3798686646e5c8d935
Source dataset
uspto-grants-1999_12
Patent number
US06001849

Reaction notes

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