Propynamide → 6-Benzyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one

HRID 1713118Notes

Reaction equation

HRID 1713118 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]=[C:11]([N:14]2[CH2:18][CH2:17][CH2:16]C2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N)(=[O:22])C#C>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]2[NH:14][C:18](=[O:22])[CH:17]=[CH:16][C:12]=2[CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 101445PropynamideHCID 117468121-Benzyl-4-(1-pyrrolidinyl)-1,2,3,6-tetrahydropyridine

Product 1

HCID 223351456-Benzyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-benzyl-4-pyrrolidin-1-yl-1,2,3,6-tetrahydropyridine (2.58 g, 10.65 mmol) in toluene (30 mL) is added propiolamide (1.47 g, 21.29 mmol) and the mixture is refluxed for 4 hr. The mixture is cooled to rt and the solvent is removed in vacuo. The residue is partitioned between NaHCO3 (30 mL) and DCM (30 mL). The layers are separated and the aqueous layer is extracted with DCM (30 ml). The combined extracts are dried and evaporated and the residue is purified by flash column with 5% MeOH in DCM to give the title compound as a light yellow solid. MS (M+1): 241.1.

Workup

  1. temperaturethe mixture is refluxed for 4 hr
  2. customthe solvent is removed in vacuo
  3. customThe residue is partitioned between NaHCO3 (30 mL) and DCM (30 mL)
  4. customThe layers are separated
  5. extractionthe aqueous layer is extracted with DCM (30 ml)
  6. customThe combined extracts are dried
  7. customevaporated
  8. customthe residue is purified by flash column with 5% MeOH in DCM

Sources & evidence

ORD record
ord-77d14153a3b94344a3ffced9f4fd8fca
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

Loading…