Benzylamine → HCID 69256693, compound

HRID 1793339Notes

Reaction equation

HRID 1793339 reaction equation
CS(O[CH2:6][C@H:7]1[O:16][C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[O:9][CH2:8]1)(=O)=O.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])(O)=O.[Na+]>O1CCOCC1>[C:18]1([CH2:17][NH:24][CH2:6][C@@H:7]2[O:16][C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[O:9][CH2:8]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 516892Sodium BicarbonateHCID 131725870HCID 131725870, compound

Product 1

HCID 69256693HCID 69256693, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of intermediate (3) (0.041 mol), benzylamine (0.041 mol) and NaHCO3 (0.11 mol) in dioxane (100 ml) was stirred and refluxed for 48 hours. The solvent was evaporated. The residue was taken up in water and DCM. The separated organic layer was dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5). The desired fractions were collected, the solvent was evaporated, yielding (S)-2,3-dihydro-N-(phenylmethyl)-[1,4]dioxino[2,3-b]pyridine-3-methanamine (intermediate 55).

Workup

  1. temperaturerefluxed for 48 hours
  2. customThe solvent was evaporated
  3. customThe separated organic layer was dried
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5)
  7. customThe desired fractions were collected
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-5e097a300e7d4722996dea0fb55be713
Source dataset
uspto-grants-2006_07
Patent number
US07081453B2

Reaction notes

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