Acetic Acid → HCID 86750863, compound

HRID 1781162Notes

Reaction equation

HRID 1781162 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][O:17][CH2:18]CN.C(O)(=O)C.C([BH3-])#[N:26].[Na+]>C(O)C>[CH3:16][O:17][CH2:18][C:14]1[CH:15]=[C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:9]=[CH:10][C:11]=1[CH2:12][NH2:26]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 80182-MethoxyethylamineHCID 661394-PhenoxybenzaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 86750863HCID 86750863, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-phenoxybenzaldehyde (1.98 g, 10 mmol) and 2-methoxyethylamine (0.751 g, 10 mmol) in ethanol (10 mL) was stirred for 1 hour. Acetic acid (1 mL) and sodium cyanoborohydride (1M in THF, 10 mL) were added, and the reaction was stirred for 14 hours. The reaction was then partitioned between ether and 10% aqueous sodium hydroxide solution. The organic layer was further washed with water and brine, dried over anhydrous potassium carbonate, filtered and concentrated. The title compound was pure as judged by NMR and was used for next step without further purification. 1H NMR (300 MHz, CDCl3) δ 7.30 (m, 4 H), 7.09 (t, 1 H), 6.98 (m, 4 H), 3.80 (s, 2 H), 3.51 (t, 2 H), 3.37 (s, 3 H), 2.51 (t, 2 H).

Workup

  1. stirringthe reaction was stirred for 14 hours
  2. customThe reaction was then partitioned between ether and 10% aqueous sodium hydroxide solution
  3. washThe organic layer was further washed with water and brine
  4. dry with materialdried over anhydrous potassium carbonate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customwas used for next step without further purification

Sources & evidence

ORD record
ord-1e8863cc88274d67b74a0a19be798263
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

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