4-Phenoxybenzaldehyde → 4-Phenoxy-N-2-propyn-1-ylbenzenemethanamine

HRID 1957327Notes

Reaction equation

HRID 1957327 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.[CH2:16]([NH2:19])[C:17]#[CH:18].C([BH3-])#N.[Na+]>C(O)(=O)C.CO>[CH2:16]([NH:19][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)[C:17]#[CH:18]

Participants

6

Reactant 3

HCID 661394-PhenoxybenzaldehydeHCID 239041PropargylamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 190694034-Phenoxy-N-2-propyn-1-ylbenzenemethanamineYield 93.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

4-Phenoxybenzaldehyde (5.0 g, 25.2 mmol) and propargylamine (1.46 g, 26.5 mmol) were dissolved in 100 mL of 1% acetic acid in methanol under an atmosphere of dry nitrogen. Sodium cyanoborohydride (1.66 g, 26.5 mmol) was added, and stirring was continued for 18 hours at which time the solvent was removed under reduced pressure. The residue was suspended in ether, washed with 5% NaHCO3 and brine, and dried over Na2 SO4 to give 5.6 g (93%) of the title compound.

Workup

  1. customthe solvent was removed under reduced pressure
  2. washwashed with 5% NaHCO3 and brine
  3. customdried over Na2 SO4

Sources & evidence

ORD record
ord-9d99493470f74abd9df6537fe794f2d5
Source dataset
uspto-grants-1998_07
Patent number
US05783593

Reaction notes

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