Hydrochloric Acid → HCID 67258281, compound

HRID 1618803Notes

Reaction equation

HRID 1618803 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]2[C:13]([NH2:14])=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[O:15]1[C:19]2[C:20]([CH:24]=O)=[CH:21][CH:22]=[CH:23][C:18]=2[CH2:17][CH2:16]1.[BH4-].[Na+].Cl>C1(C)C=CC=CC=1>[O:15]1[C:19]2[C:20]([CH2:24][NH:14][C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[O:7][C:4]3[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=3)=[CH:21][CH:22]=[CH:23][C:18]=2[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 75899Benzenamine, 2-phenoxy-HCID 27950182,3-Dihydro-1-benzofuran-7-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 67258281HCID 67258281, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

2-Aminodiphenyl ether (1 g, 5.4 mmol) was treated with 2,3-Dihydro-benzofuran-7-carbaldehyde (1 g, 7.02 mmol) and toluene (10 ml) and heated at reflux for 4 h under an atmosphere of nitrogen with vigorous stirring. The solution became yellow and homogeneous. The reaction was then concentrated in vacuum to remove the toluene, cooled to 0° C., diluted with methanol (15 ml), and treated with sodium borohydride (612 mg 16 mmol) in portions over a period of 20 min. The reaction was then allowed to warm to room temperature and stirred for a further 30 min. 2N hydrochloric acid (5 ml) was added and the reaction stirred for a further 30 min. The reaction was then concentrated in vacuum to a gum and 10% aq potassium carbonate (50 ml) added. The product was then recovered by extraction into ethyl acetate (50 ml), the extract was dried over magnesium sulphate and concentrated in vacuum to a gum. The gum was chromatographed on a 120 g silica column in a gradient of 10-30% ethyl acetate in petrol. The main fast running fraction, N-(2,3-Dihydro-benzofuran-7-ylmethyl)-N-(2-phenoxyphenyl)-amine was collected as a gum (1.2824 g, 4.04 mmole, 74.9%) that crystallized on standing.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 h under an atmosphere of nitrogen with vigorous stirring
  3. concentrationThe reaction was then concentrated in vacuum
  4. customto remove the toluene
  5. additiondiluted with methanol (15 ml)
  6. temperatureto warm to room temperature
  7. stirringthe reaction stirred for a further 30 min
  8. concentrationThe reaction was then concentrated in vacuum to a gum and 10% aq potassium carbonate (50 ml)
  9. additionadded
  10. customThe product was then recovered by extraction into ethyl acetate (50 ml)
  11. dry with materialthe extract was dried over magnesium sulphate
  12. concentrationconcentrated in vacuum to a gum
  13. customThe gum was chromatographed on a 120 g silica column in a gradient of 10-30% ethyl acetate in petrol
  14. customcrystallized

Sources & evidence

ORD record
ord-d3dbcc62bb8447908cafa4d585455228
Source dataset
uspto-grants-2014_07
Patent number
US08771641B2

Reaction notes

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