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

HRID 2197615Notes

Reaction equation

HRID 2197615 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

According 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 acetate 10 with methyl lithium followed by hydrolysis 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-766126893383466d8c1d64d4d66c1290
Source dataset
uspto-grants-2012_12
Patent number
US08338611B2

Reaction notes

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