Water → HCID 22147744, compound

HRID 2227758Notes

Reaction equation

HRID 2227758 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH2:25])=[O:24])=[CH:21]N=1.O.[CH3:29]C(N(C)C)=O>>[CH2:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][C:19]2[CH:27]=[CH:26][C:22]([C:23]([NH2:25])=[O:24])=[CH:21][CH:29]=2)=[CH:15][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 962WaterHCID 31374DimethylacetamideHCID 804566-ChloronicotinamideHCID 30425724-(2-(Benzylamino)ethyl)phenol

Product 1

HCID 22147744HCID 22147744, compound

Procedure

N-benzyl-4-hydroxyphenethylamine (J. Het. Chem., p. 839, 1971; 7.26 g, 0.032 mol) and 6-chloronicotinamide (5.0 g, 0.032 mol)were dissolved in 180 ml of dimethylacetamide and heated to reflux while water was collected in a Dean-Stark trap prefilled with isooctane. The reaction was refluxed under nitrogen for 17 hrs and additional 6-chloronicotinamide (1 g) added. After 2 hours, the solvent was removed in vacuo and the residue dissolved in 125 ml of ethyl acetate. The solution was shaken with dilute HCl and the solids collected by filteration (8.2 g). NMR.

Workup

  1. temperatureheated
  2. customwas collected in a Dean-Stark trap
  3. temperatureThe reaction was refluxed under nitrogen for 17 hrs
  4. additionadditional 6-chloronicotinamide (1 g) added
  5. customthe solvent was removed in vacuo
  6. dissolutionthe residue dissolved in 125 ml of ethyl acetate
  7. customthe solids collected by filteration (8.2 g)

Sources & evidence

ORD record
ord-587c11e6f24644eebe3cebc053641f95
Source dataset
uspto-grants-2002_07
Patent number
US06413991B1

Reaction notes

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