4-Phenoxybenzaldehyde → HCID 19069360, compound

HRID 1957329Notes

Reaction equation

HRID 1957329 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.[CH:16]1([CH2:19][NH2:20])[CH2:18][CH2:17]1.C([BH3-])#N.[Na+]>CO>[CH:16]1([CH2:19][NH:20][CH2:12][C:11]2[CH:14]=[CH:15][C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:9][CH:10]=2)[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 661394-PhenoxybenzaldehydeHCID 75646CyclopropanemethanamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 19069360HCID 19069360, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Phenoxybenzaldehyde (3.0 g, 15.1 mmol) and cyclopropylmethylamine (1.1 g, 15.1 mmol) were dissolved in methanol (85 mL) under nitrogen at room temperature. Sodium cyanoborohydride (0.95 g, 15.1 mmol) was added, and stirring was continued for 48 hours. The solvent was evaporated under reduced pressure, and the residue was suspended in ether, washed with brine, and dried over Na2SO4The ether was evaporated, and the crude product was chromatographed on silica gel eluting with 3% methanol-methylene chloride to provide 3.0 g (78%) of the title compound as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ0.08-0.15 (m, 2H), 0.45-0.55 (m, 2H), 0.93-1.05 (m, 1H), 1.45 (br s, 1H), 2.50 (d, J=7.5 Hz, 2H), 3.78 (s, 2H), 6.95-7.03 (m, 4H), 7.05-7.13 (m, 1H), 7.25-7.38 (m, 4H). MS (DCl/NH3) m/e 254 (M+H)+.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washwashed with brine
  3. dry with materialdried over Na2SO4The ether
  4. customwas evaporated
  5. customthe crude product was chromatographed on silica gel eluting with 3% methanol-methylene chloride

Sources & evidence

ORD record
ord-c651f67f7df4405fb8b5f5a51afd55dd
Source dataset
uspto-grants-1998_07
Patent number
US05783593

Reaction notes

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