Ammonia → HCID 14856314, compound

HRID 1957340Notes

Reaction equation

HRID 1957340 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([NH2:19])[CH2:17][CH3:18].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[BH4-].[Na+].N>C(O)C>[CH2:16]([NH:19][CH2:11][C:10]1[CH:13]=[CH:14][CH:15]=[C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:9]=1)[CH2:17][CH3:18]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 7852PropylamineHCID 382843-PhenoxybenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 4311764Sodium borohydride

Product 1

HCID 14856314HCID 14856314, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

3-Phenoxybenzaldehyde (2.00 mL, 2.29 g, 11.6 mmol), n-propylamine (0.95 mL, 0.68g, 11.5mmol), and p-toluenesulfonic acid monohydrate (15 mg, 0.08 mmol) were dissolved in absolute ethanol (15 mL), then heated to 80° C. in a sealed tube for 2.5 hours. The reaction was cooled to room temperature, transferred to a round-bottom flask, then sodium borohydride (440 mg, 11.6 mmol) was added, followed by heating under reflux for 2.5 hours. The reaction was concentrated, the residue was partitioned between water and EtOAc, and the EtOAc layer was washed with water and brine. After drying with Na2SO4, filtration, and concentration, the residue was purified by chromatography on silica gel using 4:6 followed by 3:7 hexane-EtOAc to give 1.59 g (57%) light yellow oil. 1H NMR (CDCl3) δ7.30 (m, 3H), 7.08 (m, 2H), 7.00 (m, 3H), 6.88 (dd, 1H), 3.77 (s, 2H), 2.60 (t, 2H), 1.53 (m, 2H), 0.92 (t, 3H). MS (DCl/NH3) m/e 242 (M+H)+.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customtransferred to a round-bottom flask
  3. temperatureby heating
  4. temperatureunder reflux for 2.5 hours
  5. concentrationThe reaction was concentrated
  6. customthe residue was partitioned between water and EtOAc
  7. washthe EtOAc layer was washed with water and brine
  8. dry with materialAfter drying with Na2SO4, filtration, and concentration
  9. customthe residue was purified by chromatography on silica gel using 4:6
  10. customto give 1.59 g (57%) light yellow oil

Sources & evidence

ORD record
ord-d3ccd80c4db24ad9a2a596f7d91ac0af
Source dataset
uspto-grants-1998_07
Patent number
US05783593

Reaction notes

Loading…