Water → HCID 778491, compound

HRID 1700837Notes

Reaction equation

HRID 1700837 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH3:11][C@H:12]([NH2:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>C1(C)C=CC=CC=1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH:1]=[N:19][C@H:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:11])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 312444-MethoxybenzaldehydeHCID 758181-Phenethylamine, (-)-

Product 1

HCID 778491HCID 778491, compoundYield 102.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of p-anisaldehyde (11.24 g, 82.5 mmol) and (S)-α methyl benzyl amine (10.0 g, 82.5 mmol) in toluene (100 mL) was heated to reflux with removal of water by a Dean-Stark apparatus. After cooling to ambient temperature, the mixture was concentrated to provide 20.15 g (100%) of the desired product. 1H NMR (300 MHz, CDCl3) δ 8.30 (s, 1H), 7.75-7.68 (m, 2H), 7.45-7.15 (m, 5H), 4.50 (q, 1H, J=6.6 Hz), 3.82 (s, 3H), 1.58 (d, 3H, J=6.6 Hz).

Workup

  1. temperaturewas heated
  2. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-1c90815f279840dba2e9195a687eaf51
Source dataset
uspto-grants-2002_02
Patent number
US06350902B2

Reaction notes

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