Propylamine → HCID 14856314, compound

HRID 1781150Notes

Reaction equation

HRID 1781150 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].[BH4-].[Na+]>C(O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[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

6

Reactant 3

HCID 7852PropylamineHCID 382843-PhenoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 14856314HCID 14856314, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

3-Phenoxybenzaldehyde (2.00 mL, 2.29 g, 11.6 mmol), n-propylamine (0.95 mL, 0.68 g, 11.5 mmol), 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, transfered 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 partitioned between water and EtOAc, the EtOAc layer washed with water and brine. After drying with Na2SO4, filtration, and concentration, the residue was purified by chromatography on silica gel eluting with 4:6 followed by 3:7 hexane-EtOAc to give 1.59 g (57%) of the title compound as a light yellow oil. 1H NMR (CDCl3) δ 7.30 (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. customtransfered to a round-bottom flask
  3. temperatureby heating
  4. temperatureunder reflux for 2.5 hours
  5. concentrationThe reaction was concentrated
  6. customthe residue partitioned between water and EtOAc
  7. washthe EtOAc layer 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 eluting with 4:6

Sources & evidence

ORD record
ord-7ea1fd831cca4e038981a8eb07c45074
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

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