4-Phenoxybenzaldehyde → HCID 53817987, compound

HRID 1957351Notes

Reaction equation

HRID 1957351 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.[C@H:16]([NH2:20])([CH2:18][CH3:19])[CH3:17].C([BH3-])#N.[Na+]>CO>[C@H:16]([NH:20][CH2:12][C:11]1[CH:14]=[CH:15][C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:9][CH:10]=1)([CH2:18][CH3:19])[CH3:17]

Participants

5

Reactant 3

HCID 661394-PhenoxybenzaldehydeHCID 2724537(R)-sec-butylamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 53817987HCID 53817987, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Phenoxybenzaldehyde (8.13 g, 41 mmol) and (R)-sec-butylamine (3 g, 41 mmol) were dissolved in methanol (137 mL) under nitrogen at room temperature. Sodium cyanoborohydride (2.58 g) was added, and stirring was continued for 18 hours. The solvent was removed, and the residue was suspended in ether, washed with brine and dried over Na2SO4. The ether was evaporated, and the crude product was chromatographed on silica gel eluting with 3% methanol in methylene chloride to provide 8.0 g (77%) of the title compound as a colorless oil.

Workup

  1. customThe solvent was removed
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customThe ether was evaporated
  5. customthe crude product was chromatographed on silica gel eluting with 3% methanol in methylene chloride

Sources & evidence

ORD record
ord-0baa1017354342078af5de1ef510927b
Source dataset
uspto-grants-1998_07
Patent number
US05783593

Reaction notes

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