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

HRID 1781141Notes

Reaction equation

HRID 1781141 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 Na2SO4 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. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-9b1496cf769e4354b5369132fdaaf338
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

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