Dimethylformamide dimethyl acetal → 3-Dimethylaminomethylene-2'-(4-methoxybenzyloxy)-2,3,5,6-tetrahydro[1,3']bipyridinyl-4-one

HRID 632824Notes

Reaction equation

HRID 632824 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][O:8][C:9]2[C:14]([N:15]3[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]3)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1.CO[CH:26](OC)[N:27]([CH3:29])[CH3:28]>>[CH3:26][N:27]([CH:29]=[C:17]1[C:18](=[O:21])[CH2:19][CH2:20][N:15]([C:14]2[C:9]([O:8][CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:23][CH:22]=3)=[N:10][CH:11]=[CH:12][CH:13]=2)[CH2:16]1)[CH3:28]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 1212495762'-(4-Methoxybenzyloxy)-2,3,5,6-tetrahydro[1,3']bipyridinyl-4-one

Product 1

HCID 1212495823-Dimethylaminomethylene-2'-(4-methoxybenzyloxy)-2,3,5,6-tetrahydro[1,3']bipyridinyl-4-one

Procedure

A solution of 2′-(4-methoxybenzyloxy)-2,3,5,6-tetrahydro[1,3′]bipyridinyl-4-one (962 mg, 3.08 mmol) in N,N-dimethylformamide-dimethylacetal (7.0 ml, 52.28 mmol) was heated at 75° C. for 21 hours. The solvent was removed in vacuo and the residue was eluted through a flash column (silica gel 60, 230-400 mesh, 8% methanol in EtOAc) to give the title compound as an orange, viscous oil (628 mg, 56%).

Workup

  1. customThe solvent was removed in vacuo
  2. washthe residue was eluted through a flash column (silica gel 60, 230-400 mesh, 8% methanol in EtOAc)

Sources & evidence

ORD record
ord-51bd6d9365024025a8289966aa1e3f6a
Source dataset
uspto-grants-2016_04
Patent number
US09321766B1

Reaction notes

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