Methanol → HCID 67258841, compound

HRID 713823Notes

Reaction equation

HRID 713823 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH2:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]1[O:25][C:24]2[C:17](=[C:18]([CH:21]=[CH:22][CH:23]=2)[CH:19]=O)[O:16]1.CO.[BH4-].[Na+]>C(O)=O>[O:25]1[C:24]2[CH:23]=[CH:22][CH:21]=[C:18]([CH2:19][NH:14][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:17]=2[O:16][CH2:15]1

Participants

6

Reactant 4

HCID 887MethanolHCID 75899Benzenamine, 2-phenoxy-HCID 822641,3-Benzodioxole-4-carboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 67258841HCID 67258841, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-phenoxy-phenylamine (410 mg, 2.22 mmol) and 2,3-(methylenedioxy)-benzaldehyde (500 mg, 3.33 mmol) was heated at 90° C. for 2 h under nitrogen. The reaction was cooled to 0° C. and MeOH (4 mL) was added, followed by NaBH4 (253 mg, 6.70 mmol) in portions over 20 min. The mixture was stirred at room temperature for 24 h. Formic acid (0.4 mL was added and the mixture stirred for 15 min. The solvents were removed in vacuo, the residue quenched with saturated aqueous NaHCO3 (50 mL), extracted with DCM (2×30 mL), dried over MgSO4, filtered and solvents removed in vacuo. The crude material was purified by silica gel chromatography eluting with petroleum spirit (A) and ethyl acetate (B) (5% B, 80 g, 4.0 CV, 60 mL/min) to afford 360 mg (51%) of N-(benzo[1,3]dioxol-4-ylmethyl)-N-(2-phenyloxy-phenyl) amine as a white solid.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. stirringthe mixture stirred for 15 min
  3. customThe solvents were removed in vacuo
  4. customthe residue quenched with saturated aqueous NaHCO3 (50 mL)
  5. extractionextracted with DCM (2×30 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customsolvents removed in vacuo
  9. customThe crude material was purified by silica gel chromatography
  10. washeluting with petroleum spirit (A) and ethyl acetate (B) (5% B, 80 g, 4.0 CV, 60 mL/min)

Sources & evidence

ORD record
ord-e057f36020754c67a99f0479ab961abe
Source dataset
uspto-grants-2015_11
Patent number
US09186424B2

Reaction notes

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