Hydrochloric Acid → 4-(2-hydroxyethyl)-N-(4-methoxybenzyl)nicotinamide

HRID 1844003Notes

Reaction equation

HRID 1844003 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.[C:11]1(=[O:21])[C:16]2=[CH:17][N:18]=[CH:19][CH:20]=[C:15]2[CH2:14][CH2:13][O:12]1.CO.Cl>C1COCC1.C(Cl)(Cl)Cl>[OH:12][CH2:13][CH2:14][C:15]1[C:16]([C:11]([NH:10][CH2:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[O:21])=[CH:17][N:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 754524-MethoxybenzylamineHCID 442532Gentianadine

Product 1

HCID 668036304-(2-hydroxyethyl)-N-(4-methoxybenzyl)nicotinamideYield 103.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(4-Methoxyphenyl) methanamine (6.57 mL, 50.676 mmol) was added to a solution of 3,4-dihydro-1H-pyrano[3,4-c]pyridin-1-one (I-65c: 750 mg, 5.068 mmol) in THF (15 mL) and the resulting reaction mass was refluxed for 48 hours. The reaction was monitored by TLC (10% methanol in CHCl3). The reaction mass was cooled to 0° C., neutralized with 1N HCl and extracted using DCM. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford 1.5 g of the product.

Workup

  1. customthe resulting reaction mass
  2. temperaturewas refluxed for 48 hours
  3. extractionextracted
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-efb2f11af46d46a2a4ea1b25c15fcf24
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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