2-Amino-1-(3-chlorophenyl)ethan-1-ol → N-[3-(4-Methylphenyl)-1-methylpropyl]-2-hydroxy-2-(3-chlorophenyl)ethanamine

HRID 280303Notes

Reaction equation

HRID 280303 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=O)[CH3:11])=[CH:4][CH:3]=1.[Cl:13][C:14]1[CH:15]=[C:16]([CH:20]([OH:23])[CH2:21][NH2:22])[CH:17]=[CH:18][CH:19]=1>C1C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]([NH:22][CH2:21][CH:20]([OH:23])[C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([Cl:13])[CH:15]=2)[CH3:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 54639084-(p-Tolyl)-2-butanone

Product 1

HCID 23322179N-[3-(4-Methylphenyl)-1-methylpropyl]-2-hydroxy-2-(3-chlorophenyl)ethanamine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4-(4-Methylphenyl)butan-2-one (1.62 g) and 2-(3-chlorophenyl)-2-hydroxyethanamine (1.71 g) was refluxed in benzene under Dean & Stark conditions for 4 h. The solvent was removed under reduced pressure, replaced with methanol (100 ml) and sodium borohydride (2 g) added portionwise. The solvent was evaporated under reduced pressure, the residue partitioned between water and ether and the ether layer dried (MgSO4). Removal of the solvent gave an oil which was chromatographed on Kieselgel 60. Elution with 1% methanol-chloroform gave the title compound as an 11:89 mixture of diastereoisomers, mp 75-106 (hexane).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionadded portionwise
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue partitioned between water and ether
  5. dry with materialthe ether layer dried (MgSO4)
  6. customRemoval of the solvent
  7. customgave an oil which
  8. customwas chromatographed on Kieselgel 60
  9. washElution with 1% methanol-chloroform

Sources & evidence

ORD record
ord-d6084b572ab14f168a71bb533a351aeb
Source dataset
uspto-grants-1986_05
Patent number
US04588749

Reaction notes

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