Potassium Carbonate → HCID 53708317, compound

HRID 1110716Notes

Reaction equation

HRID 1110716 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 53708317HCID 53708317, compound

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-703896154d4a4439804600f427aca78e
Source dataset
uspto-grants-1990_12
Patent number
US04977148

Reaction notes

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