Benzaldehyde → 2-[2-Amino-4-(benzylamino)phenoxy]ethanol

HRID 1791085Notes

Reaction equation

HRID 1791085 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([NH2:12])[CH:9]=[CH:8][C:3]=1[O:4][CH2:5][CH2:6][OH:7].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.B.O1CCCC1>CO.O1CCCC1>[NH2:1][C:2]1[CH:11]=[C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:9]=[CH:8][C:3]=1[O:4][CH2:5][CH2:6][OH:7]

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 479332-(2,4-Diaminophenoxy)ethanolHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 220265492-[2-Amino-4-(benzylamino)phenoxy]ethanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.66 g (10 mmol) of 2-(2,4-diaminophenoxy)ethanol and 1.06 g (10 mmol) of benzaldehyde were dissolved in methanol (dried over molecular sieve). After addition of 10 mg of molecular sieve, the reaction mixture was allowed to agitate 7 hours. Then, 20 mL of a solution of borane-tetrahydrofuran com-plex (1 M in tetrahydrofuran) was added at 0° C., and the reaction mixture was allowed to agitate one hour at room temperature. At the end of the reaction, the reaction mixture was filtered and hydrolyzed. The precipitate was filtered off, washed with water and then dried.

Workup

  1. additionAfter addition of 10 mg of molecular sieve
  2. stirringto agitate one hour at room temperature
  3. customAt the end of the reaction
  4. filtrationthe reaction mixture was filtered
  5. filtrationThe precipitate was filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-07a7655d22c44b9194cd699db25c9830
Source dataset
uspto-grants-2006_07
Patent number
US07074243B2

Reaction notes

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