Benzaldehyde → 4-(2-(Benzylamino)ethyl)phenol

HRID 2224680Notes

Reaction equation

HRID 2224680 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CO>[BH4-].[Na+]>[CH2:11]([NH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 887MethanolHCID 5610Tyramine

Product 1

HCID 30425724-(2-(Benzylamino)ethyl)phenol

Reagents, catalysts & solvents 1

HCID 4311764Sodium borohydrideSolvent

Procedure

Accordiong to Scheme 2, tyramine is treated with benzaldehyde in sodium borohydride, molecular sieves, and methanol to produce the reductive amination product 4-(benzylamino-ethyl)-phenol (8). The phenol 8 is treated with cesium carbonate and 4-fluorobenzonitrile in DMF to yield the corresponding biarylether 9. The nitrile functionality of the biaryl ether may be converted to the actetate 10 with methyl lithium followed by hydrolyis in aqueous sulfuric acid. The acetate 10 is oxidized with MCPBA to yield acetic acid 4-[4-(2-benzylamino-ethyl)-phenoxy]-phenyl ester (11).

Sources & evidence

ORD record
ord-0c7f19b828454c409f974bea9441956d
Source dataset
uspto-grants-2008_05
Patent number
US07378448B2

Reaction notes

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