Triethylamine → HCID 14371870, compound

HRID 1381951Notes

Reaction equation

HRID 1381951 reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][C:12]([CH2:18][C:19]([OH:21])=O)([C:15]([OH:17])=O)[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1(N=C=NC2CCCCC2)CCCCC1.Cl.[CH2:38]([O:45][NH2:46])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(N(CC)CC)C>CN(C)C=O>[CH2:2]([N:9]1[CH2:10][CH2:11][C:12]2([C:15](=[O:17])[N:46]([O:45][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:19](=[O:21])[CH2:18]2)[CH2:13][CH2:14]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 102312Benzyloxyamine hydrochlorideHCID 21275440HCID 21275440, compound

Product 1

HCID 14371870HCID 14371870, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1-benzyl-4-carboxypiperidin-4-yl)acetic acid.hydrochloride (31.3 g) in dimethylformamide (200 ml) was added dicyclohexylcarbodiimide (20.6 g). The mixture was stirred for one hour at room temperature, to which were added benzyloxyamine hydrochloride (16 g) and triethylamine (14 ml). The mixture was stirred for further one hour at room temperature, followed by evaporating off the solvent under reduced pressure. To the residue were added acetic anhydride (150 ml) and sodium acetic anhydride (21 g). The mixture was stirred for one hour at 100° C., then insolubles were filtered off, and the solvent was evaporated off under reduced pressure. To the residue was added ethyl acetate (200 ml), to which was further added a saturated aqueous solution of sodium hydrogencarbonate until the aqueous layer became alkaline. The organic layer was washed with water, dried over anhydrous magnesium sulfate, followed by evaporating off the solvent under reduced pressure. To the residual oil was added 100 ml of acetonitrile, and insolubles were filtered off. Acetonitrile was evaporated off, and the residue was recrystallized from acetonitrile-ethyl ether to obtain 16.5 g of a colorless solid, m.p. 146° to 152° C.

Workup

  1. stirringThe mixture was stirred for further one hour at room temperature
  2. customby evaporating off the solvent under reduced pressure
  3. additionTo the residue were added acetic anhydride (150 ml) and sodium acetic anhydride (21 g)
  4. stirringThe mixture was stirred for one hour at 100° C.
  5. filtrationinsolubles were filtered off
  6. customthe solvent was evaporated off under reduced pressure
  7. additionTo the residue was added ethyl acetate (200 ml)
  8. additionto which was further added a saturated aqueous solution of sodium hydrogencarbonate until the aqueous layer
  9. washThe organic layer was washed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customby evaporating off the solvent under reduced pressure
  12. additionTo the residual oil was added 100 ml of acetonitrile, and insolubles
  13. filtrationwere filtered off
  14. customAcetonitrile was evaporated off
  15. customthe residue was recrystallized from acetonitrile-ethyl ether

Sources & evidence

ORD record
ord-edea2e3dcaa0453ba2101310d2b1c0ab
Source dataset
uspto-grants-1989_02
Patent number
US04804665

Reaction notes

Loading…