Benzene → HCID 18628102, compound

HRID 280304Notes

Reaction equation

HRID 280304 reaction equation
[OH:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[F:11])[CH2:3][NH2:4].C[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20](=O)[CH3:21])=[CH:15][CH:14]=1.[CH:23]1C=CC=CC=1>>[CH3:23][C:15]1[CH:14]=[CH:13][CH:18]=[CH:17][C:16]=1[CH2:19][CH:20]([NH:4][CH2:3][CH:2]([OH:1])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[F:11])[CH3:21]

Participants

4

Reactant 3

HCID 241BenzeneHCID 1374281-(4-Methylphenyl)propan-2-oneHCID 150671762-Amino-1-(2-fluorophenyl)ethan-1-ol

Product 1

HCID 18628102HCID 18628102, compound

Procedure

A mixture of 2-hydroxy-2-(2-fluorophenyl)ethanamine (1.54 g) and 4-methylphenylacetone (1.48 g) was refluxed in benzene (70 ml) under Dean & Stark conditions for 4h. The solvent was removed under reduced pressure, replaced with methanol and sodium borohydride (3 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 under reduced pressure gave an oil which was chromatographed on Kieselgel 60. Elution with 1% methanol-chloroform gave the title compound (1.58 g) as a 49:51 mixture of diastereoisomers, mp 65-68 (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 under reduced pressure
  7. customgave an oil which
  8. customwas chromatographed on Kieselgel 60
  9. washElution with 1% methanol-chloroform

Sources & evidence

ORD record
ord-3818f24feece47d59ec5bd4e83349171
Source dataset
uspto-grants-1986_05
Patent number
US04588749

Reaction notes

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