Sodium Bicarbonate → 1-Methyl-7-(3-pyridyl)-1,7-diazaspiro[4.4]nonane

HRID 967926Notes

Reaction equation

HRID 967926 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:15][CH2:14][C:9]3([NH:13][CH2:12][CH2:11][CH2:10]3)[CH2:8]2)[CH:2]=1.[C:16](=O)(O)[O-].[Na+]>C(O)=O.C=O>[CH3:16][N:13]1[C:9]2([CH2:14][CH2:15][N:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH2:8]2)[CH2:10][CH2:11][CH2:12]1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 101766077-(3-Pyridinyl)-1,7-diazaspiro[4.4]nonane

Product 1

HCID 103309741-Methyl-7-(3-pyridyl)-1,7-diazaspiro[4.4]nonaneYield 93.6%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 712FormaldehydeSolvent

Procedure

7-(3-Pyridyl)-1,7-diazaspiro[4.4]nonane (30 mg, 0.15 mmol) was dissolved in 98% formic acid (0.5 mL) and formaldehyde (1 mL, 28% aqueous solution). The reaction mixture was heated to reflux for 8 h. The reaction mixture was cooled to room temperature, basified with saturated aqueous sodium bicarbonate to pH 9-10 and extracted with chloroform (4×3 mL). The combined chloroform extracts were dried (K2CO3), filtered and concentrated on a rotary evaporator to afford 30 mg of the desired compound (93.6%) as a light brown liquid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 8 h
  3. extractionextracted with chloroform (4×3 mL)
  4. dry with materialThe combined chloroform extracts were dried (K2CO3)
  5. filtrationfiltered
  6. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-3f55978e97444ab8836270d45e64e422
Source dataset
uspto-grants-2005_10
Patent number
US06956042B2

Reaction notes

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