3-Methoxyphenethylamine → HCID 19069351, compound

HRID 1781166Notes

Reaction equation

HRID 1781166 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4]C=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=1)[CH2:22][CH2:23][NH2:24].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[BH4-].[Na+]>C(O)C>[O:8]([C:9]1[CH:10]=[CH:11][C:12]([CH2:13][NH:24][CH2:23][CH2:22][C:21]2[CH:25]=[CH:26][CH:27]=[C:19]([O:18][CH3:17])[CH:20]=2)=[CH:15][CH:16]=1)[C:1]1[CH:2]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 748663-MethoxyphenethylamineHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 521998p-Toluenesulfonic acid monohydrateHCID 4311764Sodium borohydride

Product 1

HCID 19069351HCID 19069351, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-benzoxybenzaldehyde (2.5 g, 12.6 mmol), 3-methoxyphenethylamine (1.9 g, 12.6 mmol), a catalytic amount of p-toluenesulfonic acid monohydrate in absolute ethanol (12 mL) was stirred at 80° C. for 1.5 hours. After cooling to room temperature, NaBH4 (0.49 g, 13.0 mmol) was added in portions. The reaction mixture was stirred at 80° C. for 1 hour, then cooled to room temperature, and the ethanol was removed in vacuo. Water was added to the residue and the mixture was extracted with ethyl acetate. The combined extracts were washed with saturated NaCl, dried over MgSO4, filtered, and the solvent removed in vacuo to afford a colorless oil which was purified by silica gel chromatography eluting with 20% ethyl acetate in hexane saturated with NH3 to afford the title compound (3.2 g, 76%) as a colorless oil. MS (DCl/NH3) m/e 334 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ 2.82 (t, 2H), 2.92 (t, 2H), 3.77 (s, 2H), 3.80 (s, 3H), 6.80 (m, 3H), 6.98 (m, 3H), 6.08 (t, 1H), 7.22 (m, 3H), 7.32 (t, 2H).

Workup

  1. temperaturecooled to room temperature
  2. customthe ethanol was removed in vacuo
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe combined extracts were washed with saturated NaCl
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customto afford a colorless oil which
  10. customwas purified by silica gel chromatography
  11. washeluting with 20% ethyl acetate in hexane saturated with NH3

Sources & evidence

ORD record
ord-101e2eade719414ba492ff8051d17790
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

Loading…