Potassium Carbonate → N-benzyl-N-(2-p-hydroxyphenoxyethyl)-3-o-fluorophenoxy-2-hydroxypropylamine

HRID 1651123Notes

Reaction equation

HRID 1651123 reaction equation
Cl.[CH2:2]([NH:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:20]1[CH:22]([CH2:23][O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])[CH2:21]1.C(=O)([O-])[O-].[K+].[K+]>CC(O)C>[CH2:2]([N:9]([CH2:21][CH:22]([OH:20])[CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[F:31])[CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27060715620-80-1HCID 22154105HCID 22154105, compound

Product 1

HCID 53708317N-benzyl-N-(2-p-hydroxyphenoxyethyl)-3-o-fluorophenoxy-2-hydroxypropylamine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of N-benzyl-2-(p-hydroxyphenoxy)ethylamine hydrochloride (see Example 1) (5.6 g), 1,2-epoxy-3-o-fluorophenoxypropane (3.6 g) and anhydrous potassium carbonate (2.7 g) was heated under reflux in propan-2-ol (100 ml) for 24 hours. The reaction mixture was cooled, the solid removed by filtration and the solvent evaporated from the filtrate. The residual oil was purified by chromatography on silica eluting with 1% v/v methanol in dichloromethane to give N-benzyl-N-(2-p-hydroxyphenoxyethyl)-3-o-fluorophenoxy-2-hydroxypropylamine as a colourless oil; NMR: 2.27-3.15 (m, 4H, CH2NCH2), 3.8 (dd,2H, NCH2Ph), 3.9-4.2 (m,5H, OCH2.CHOH, o-F-Ph.OCH2), 6.7 (s, 4 aromatic H), 6.8-7.1 (m, 4 aromatic H), 7.3 (m,5H, CH2Ph).

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled
  3. customthe solid removed by filtration
  4. customthe solvent evaporated from the filtrate
  5. customThe residual oil was purified by chromatography on silica eluting with 1% v/v methanol in dichloromethane

Sources & evidence

ORD record
ord-7b22f9db564245aba297fa09d94d5660
Source dataset
uspto-grants-1990_05
Patent number
US04927836

Reaction notes

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