Water → HCID 67166273, compound

HRID 553321Notes

Reaction equation

HRID 553321 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=O.[NH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1.O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[N:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[CH2:20][CH2:19][NH:18][CH2:13][C:12]1[CH:15]=[CH:16][CH:17]=[C:10]([CH2:9][CH2:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[CH:11]=1

Participants

6

Reactant 3

HCID 962WaterHCID 759192-PyridineethanamineHCID 866183253-[2-(Tetrahydropyran-2-yloxy)-ethyl]-benzaldehyde

Product 1

HCID 67166273HCID 67166273, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 3-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-benzaldehyde (Example 50, step A, 6.1 g) and 2-(2-aminoethyl)pyridine (3.18 g, 3.1 ml) in toluene (150 mL) was added p-toluene sulfonic acid (100 mg). The reaction was heated at reflux in a Dean-Stark apparatus for couple of hours. Around 2 mL water were displaced. The mixture was cooled and washed with aqueous bicarbonate and concentrated in vacuo. The residue was taken up in ethanol (100 ml) and cooled. Sodium borohydride (1.0 g) was added slowly and the reaction left 1 hour to warm to room temperature. Water was added (100 mL) and ethanol removed by distillation. The reaction was partitioned between aqueous bicarbonate and ethyl acetate. The organic layers were dried over sodium sulfate and concentrated in vacuo to give yellow oil (6.5 g). The material was used in the next step without further purification.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux in a Dean-Stark apparatus for couple of hours
  3. temperatureThe mixture was cooled
  4. washwashed with aqueous bicarbonate
  5. concentrationconcentrated in vacuo
  6. temperaturecooled
  7. additionSodium borohydride (1.0 g) was added slowly
  8. additionWater was added (100 mL) and ethanol
  9. customremoved by distillation
  10. customThe reaction was partitioned between aqueous bicarbonate and ethyl acetate
  11. dry with materialThe organic layers were dried over sodium sulfate
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a13ba79c7160460ebab134b8396297d2
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Reaction notes

Loading…