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

HRID 632831Notes

Reaction equation

HRID 632831 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][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)=[C:13]([CH3:22])[CH:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1.CO[CH:27](OC)[N:28]([CH3:30])[CH3:29]>>[CH3:27][N:28]([CH:30]=[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:24][CH:23]=3)=[N:10][CH:11]=[CH:12][C:13]=2[CH3:22])[CH2:16]1)[CH3:29]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 1212495972'-(4-Methoxybenzyloxy)-4'-methyl-2,3,5,6-tetrahydro[1,3']bipyridinyl-4-one

Product 1

HCID 1212495693-Dimethylaminomethylene-2'-(4-methoxybenzyloxy)-4'-methyl-2,3,5,6-tetrahydro[1,3']bipyridinyl-4-one

Conditions

Temperature
100 °C

Procedure

A mixture of 2′-(4-Methoxybenzyloxy)-4′-methyl-2,3,5,6-tetrahydro[1,3′]bipyridinyl-4-one (6.40 g, 19.61 mmol) in N,N-dimethylformamide-dimethylacetal (44.63 ml, 333.37 mmol) from a freshly opened bottle was heated at 100° C. for 48 hours. The solvent was removed in vacuo and the residue was eluted through a flash column (silica gel 60, 230-400 mesh, EtOAc to 8% methanol in EtOAc) to give title compound as an orange, viscous oil which slowly solidified on standing (5.21 g, 70%).

Workup

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

Sources & evidence

ORD record
ord-275ffb01b94349efa1dcfcabeb42bed5
Source dataset
uspto-grants-2016_04
Patent number
US09321766B1

Reaction notes

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