Phenethylamine → 7-hydroxymethyl-4-isopropyl-2-[3-(N-methyl-N-phenethylamino)propoxy]-2,4,6-cycloheptatrien-1-one

HRID 234164Notes

Reaction equation

HRID 234164 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:7](=[O:18])[C:8]([CH2:16][OH:17])=[CH:9][CH:10]=[C:11]([CH:13]([CH3:15])[CH3:14])[CH:12]=1.[CH2:19]([NH2:27])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH2:28](N(CC)CC)C>C(Cl)(Cl)Cl.ClCCl>[OH:17][CH2:16][C:8]1[C:7](=[O:18])[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:27]([CH3:28])[CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:12][C:11]([CH:13]([CH3:15])[CH3:14])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 214599293-Bromopropoxy-7-hydroxymethyl 4-isopropyl-2,4,6-cycloheptatrien-1-one

Product 1

HCID 214599567-hydroxymethyl-4-isopropyl-2-[3-(N-methyl-N-phenethylamino)propoxy]-2,4,6-cycloheptatrien-1-oneYield 74%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

2-(3-bromopropoxy-7-hydroxymethyl-4-isopropyl-2,4,6-cycloheptatrien-1-one (280 mg, 0.89 mmol), N-phenethylamine (0.15 ml, 1.03 mmol), triethylamine (0.15 ml, 1.08 mmol) were dissolved in chloroform (5 ml), and the solution was heated and refluxed for 5 hours. The solution was diluted with dichloromethane, washed with water and dried over sodium sulfate. After solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography [eluent:chloroform/methanol (10:1)] to give 242 mg of 7-hydroxymethyl-4-isopropyl-2-[3-(N-methyl-N-phenethylamino)propoxy]-2,4,6-cycloheptatrien-1-one as a yellowish brown oil (yield: 74%).

Workup

  1. temperaturethe solution was heated
  2. temperaturerefluxed for 5 hours
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. distillationAfter solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography [eluent:chloroform/methanol (10:1)]

Sources & evidence

ORD record
ord-72e3eb4b622c4593a5602a7ea86dce94
Source dataset
uspto-grants-1997_01
Patent number
US05594144

Reaction notes

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