Phenylethanolamine → N-[2-(4-Carboxyphenyl)-1-methylethyl]-2-hydroxy-2-phenylethanamine

HRID 580624Notes

Reaction equation

HRID 580624 reaction equation
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][NH2:4].[C:11]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28](=O)[CH3:29])=[CH:23][CH:22]=1)([O:13]CC1C=CC=CC=1)=[O:12]>C1C=CC=CC=1>[C:11]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH:28]([NH:4][CH2:3][CH:2]([OH:1])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:29])=[CH:23][CH:22]=1)([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 1000PhenylethanolamineHCID 201342441-(4-Carbobenzyloxyphenyl)propan-2-one

Product 1

HCID 10108768N-[2-(4-Carboxyphenyl)-1-methylethyl]-2-hydroxy-2-phenylethanamine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-Hydroxy-2-phenylethanamine (0.68 g) and 1-(4-carbobenzyloxyphenyl)propan-2-one (1.34 g) were refluxed in benzene (50 ml) in a Dean and Stark apparatus for 2 hours. The solvent was removed, tetrahydrofuran (50 ml), benzene (10 ml) and water (3 ml) were added followed by sodium borohydride (0.9 g). The reaction mixture was left at room temperature overnight. The solvent was removed under reduced pressure and the residue partitioned between water and ether. The layers were separated and the organic layer dried (MgSO4). Removal of the solvent gave the title compound as the benzyl ester (1.67 g). This was dissolved in ethanol amd hydrogenated at 75 psi and 50° for 4 hours. Filtration and evaporation of the solvent gave the title compound mp 180°-190° (ethyl acetate-methanol). τ (TFA-d) 8.5 (3H, d, J=7 Hz), 5.85-7.45 (5H, m), 4.72 (1H, broad), 2.6 (7H, m), 1.8 (2H, d, J=8 Hz). τ (d6DMSO+D2O+NaOD) 9.05 (3H, d, J=7 Hz), 6.9-7.7 (5H, m), 2.85 (2H, d, J=8 Hz), 2.7 (5H, s), 2.17 (2H, d, J=8 Hz).

Workup

  1. customThe solvent was removed
  2. additiontetrahydrofuran (50 ml), benzene (10 ml) and water (3 ml) were added
  3. customThe solvent was removed under reduced pressure
  4. customthe residue partitioned between water and ether
  5. customThe layers were separated
  6. dry with materialthe organic layer dried (MgSO4)
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-15cc149542ce45819c3b9c94e41d44fb
Source dataset
uspto-grants-1988_06
Patent number
US04753962

Reaction notes

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