Potassium Carbonate → HCID 90417171, compound

HRID 1484822Notes

Reaction equation

HRID 1484822 reaction equation
Cl[CH2:2][C:3]1[CH2:4][N:5]([C:15](=[O:17])[CH3:16])[CH2:6][CH2:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[C:20]=1[CH:21]=[O:22].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[C:15]([N:5]1[CH2:6][CH2:7][C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:3]([CH2:2][O:18][C:19]2[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[C:20]=2[CH:21]=[O:22])[CH2:4]1)(=[O:17])[CH3:16]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 102858012,6-DihydroxybenzaldehydeHCID 90416548HCID 90416548, compound

Product 1

HCID 90417171HCID 90417171, compoundYield 18.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(3-(chloromethyl)-4-phenyl-5,6-dihydropyridin-1(2H)-yl)ethanone (100 mg, 0.40 mmol) and 2,6-dihydroxybenzaldehyde (110 mg, 0.80 mmol) in DMF (2.5 mL) was added K2CO3 (170 mg, 1.20 mmol), after heated at 50 degree for 2 h, the reaction was diluted with EtOAc, organic layer was separated and aqueous layer was extracted with EtOAc. EtOAc layers were combined, washed with Sat. NaHCO3, brine, dried over Na2SO4, and was concentrated to give crude oil, which was purified by preparative HPLC (eluted with ACN/H2O) to give 2-((1-acetyl-4-phenyl-1,2,5,6-tetrahydropyridin-3-yl)methoxy)-6-hydroxybenzaldehyde (26 mg). 1H NMR (400 MHz, CDCl3, NMR shows rotamers exist, only one set of signal was reported) δ (ppm) 11.97 (s, 1H), 10.34 (s, 1H), 7.34 (m, 4H), 7.17 (m, 2H), 6.49 (d, J=8.0 Hz, 1H), 6.11 (d, J=8.8 Hz, 1H), 4.48 (s, 2H), 4.33 (s, 2H), 3.69 (t, J=6.0 Hz, 2H), 2.55 (m, 2H), 2.18 (s, 3H); MS (ESI) m/z 352.3 [M+H]+.

Workup

  1. temperatureafter heated at 50 degree for 2 h
  2. customwas separated
  3. extractionaqueous layer was extracted with EtOAc
  4. washwashed with Sat. NaHCO3, brine
  5. dry with materialdried over Na2SO4
  6. concentrationwas concentrated
  7. customto give crude oil, which
  8. customwas purified by preparative HPLC (eluted with ACN/H2O)

Sources & evidence

ORD record
ord-c3f6d09dfed744bbb790f64cdd82530d
Source dataset
uspto-grants-2016_08
Patent number
US09422279B2

Reaction notes

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