Benzaldehyde → 3-(2-Benzylaminoethyl)-phenol

HRID 2248138Notes

Reaction equation

HRID 2248138 reaction equation
O1CCCCC1OC1CCCCO1.[NH2:14][CH2:15][CH2:16][C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1.[CH:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[BH4-].[Na+]>C(O)C>[CH2:24]([NH:14][CH2:15][CH2:16][C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 11492m-TyramineHCID 263182Tetrahydropyranyl etherHCID 4311764Sodium borohydride

Product 1

HCID 198055723-(2-Benzylaminoethyl)-phenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 17.6 g. (79.6 mMol) tetrahydropyran-2-yl ether of 3-(2-aminoethyl)-phenol, 150 ml. ethanol and 8.9 g. (83.5 mMol) benzaldehyde is stirred for 1 hour at ambient temperature, 3.5 g. (92 mMol) sodium borohydride are added thereto at 0° C. with vigorous stirring and the reaction allowed to continue for 1 hour at 0° C. and for 1 hour at ambient temperature. The reaction mixture is then evaporated in a vacuum and the residue mixed with diethyl ether and water. After shaking up, the ethereal phase is separated off, dried with anhydrous sodium sulphate and mixed dropwise with concentrated sulphuric acid. The precipitated sulphate is dissolved in water, some 2N hydrochloric acid is added thereto, followed by heating on a waterbath for 10 minutes and cooling. By the addition of sodium carbonate, the base is liberated. It is extracted with diethyl ether, the ethereal solution is dried with anhydrous sodium sulphate and evaporated. Yield 15.0 g. (83% of theory); m.p. 86°-88° C.

Workup

  1. additionA mixture of 17.6 g
  2. customThe reaction mixture is then evaporated in a vacuum
  3. additionthe residue mixed with diethyl ether and water
  4. stirringAfter shaking up
  5. customthe ethereal phase is separated off
  6. dry with materialdried with anhydrous sodium sulphate
  7. additionmixed dropwise with concentrated sulphuric acid
  8. dissolutionThe precipitated sulphate is dissolved in water
  9. additionsome 2N hydrochloric acid is added
  10. temperatureby heating on a waterbath for 10 minutes
  11. temperaturecooling
  12. additionBy the addition of sodium carbonate
  13. extractionIt is extracted with diethyl ether
  14. dry with materialthe ethereal solution is dried with anhydrous sodium sulphate
  15. customevaporated

Sources & evidence

ORD record
ord-43025aa52c3e4ad483fbae57c416ccef
Source dataset
uspto-grants-1991_08
Patent number
US05037990

Reaction notes

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