Formic Acid → HCID 18694214, compound

HRID 581818Notes

Reaction equation

HRID 581818 reaction equation
C(O)=O.[CH2:4]=O.[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]2[CH:17]3[CH2:18][CH2:19][CH:14]([CH2:15][CH2:16]3)[NH:13]2)[CH:7]=1.[OH-].[Na+]>O>[CH3:4][N:13]1[CH:12]([C:8]2[CH:7]=[N:6][CH:11]=[CH:10][CH:9]=2)[CH:17]2[CH2:18][CH2:19][CH:14]1[CH2:15][CH2:16]2

Participants

6

Reactant 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 15383498HCID 15383498, compound

Product 1

HCID 18694214HCID 18694214, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Formic acid (5 mL, 95-97%) and formaldehyde (0.5 mL, 37%) were added to 3-(3-pyridyl)-2-azabicylo[2.2.2]octane (XIII) (170 mg) and refluxed for 24 hours under N2. The reaction mixture was cooled to 0° C. (ice bath), basified by addition of a solution of 40% w/v NaOH in water (pH=9) and extracted with chloroform (4×10 mL). The combined extracts were dried over anhydrous K2CO3, filtered and concentrated. The resulting oil was purified by distillation under reduced pressure (116°-118° C./0.4 mm Hg) to give 160 mg (88%) of (+/-)-2-methyl-3-(3-pyridyl)-2-azabicylo[2.2.2]octane (XV). 1H NMR(CDCl3): δ 8.85 (s, 1H), 8.80-8.10 (d, 1H), 7.78-7.71 (m, 1H), 7.23-7.20 (m, 1H),4.70 (s, 1H), 3.60 (s, 1H), 2.5 (s, 3H), 2.25 (s, 1H), 2.20-1.95 (m, 2H), 1.80-1.69 (m, 3H), 1.50-1.42 (m, 3H).

Workup

  1. temperaturerefluxed for 24 hours under N2
  2. additionbasified by addition of a solution of 40%
  3. extractionextracted with chloroform (4×10 mL)
  4. dry with materialThe combined extracts were dried over anhydrous K2CO3
  5. filtrationfiltered
  6. concentrationconcentrated
  7. distillationThe resulting oil was purified by distillation under reduced pressure (116°-118° C./0.4 mm Hg)

Sources & evidence

ORD record
ord-edf02bb8086b4a08be0389f8a033559f
Source dataset
uspto-grants-1999_07
Patent number
US05922723

Reaction notes

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