Formic Acid → HCID 70099645, compound

HRID 1416659Notes

Reaction equation

HRID 1416659 reaction equation
[ClH:1].Cl.[NH:3]1[CH2:7][CH2:6][CH2:5][C@H:4]1[CH2:8][CH2:9][O:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.[CH:17](O)=O>C=O>[ClH:1].[ClH:1].[CH3:17][N:3]1[CH2:7][CH2:6][CH2:5][C@H:4]1[CH2:8][CH2:9][O:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 70083023HCID 70083023, compound

Product 1

HCID 70099645HCID 70099645, compound

Reagents, catalysts & solvents 1

HCID 712FormaldehydeSolvent

Procedure

A 400 mg sample of 3-(2-(2-(S)-pyrrolidinyl)ethoxy)pyridine dihydrochloride, from Example 102 above, was dissolved in 14 mL of 37% HCHO, 14 mL of HCOOH was added, and the reaction mixture was stirred at reflux for 2.5 hours. The solution was washed with ether, adjusted to basic pH with K2CO3 and extracted with methylene chloride. The extract was dried over MgSO4 and concentrated. The residue was purified on a column of silica gel, eluting with 10% methanol in methylene chloride. The compound was converted to the salt by the HCl in ether according to Example 14c to afford the title compound. MS (DCI/NH3) m/e: 207 (M+H)+. 1H NMR (D2O, 300 MHz) δ: 1.71-1.98 (m, 1H), 2.00-2.23 (m, 3H), 2.37-2.45 (m, 1H), 2.50-2.63 (m, 1H), 2.98 (s, 3H), 3.13-3.25 (m, 1H), 3.53-3.67 (m, 1H), 3.68-3.78 (m, 1H), 4.31-4.48 (m, 2H), 8.00 (dd, J=11.0, 7.0 Hz, 1H), 8.20 (dd, J=10.5, 5.0 Hz, 1H), 8.42 (d, J=6.5 Hz, 1H), 8.50 (d, J=5.0 Hz, 1H). Anal. Calc. for C12H18N2OF·1.9 HCl·1.1 H2O: C, 48.49; H, 7.46; N, 9,42; Found C, 48.51; H, 7.69; N, 9.61. [α]25D =+36.2820 (C=0.5, H2O).

Workup

  1. temperatureat reflux for 2.5 hours
  2. washThe solution was washed with ether
  3. extractionextracted with methylene chloride
  4. dry with materialThe extract was dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified on a column of silica gel
  7. washeluting with 10% methanol in methylene chloride

Sources & evidence

ORD record
ord-c0df98876e474b7385e215e7823ea009
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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