Benzene → alpha-{1-Methyl-1-[(2-phenylethyl)amino]-ethyl}benzenemethanol

HRID 443732Notes

Reaction equation

HRID 443732 reaction equation
[NH2:1][C:2]([CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[OH:6])([CH3:4])[CH3:3].[C:13]1([CH2:19][CH:20]=O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1C=CC=CC=1>O>[CH3:3][C:2]([CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[OH:6])([NH:1][CH2:20][CH2:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:4]

Participants

5

Reactant 3

HCID 241BenzeneHCID 998PhenylacetaldehydeHCID 26760alpha-(1-Amino-1-methylethyl)benzenemethanol

Product 1

HCID 12570789alpha-{1-Methyl-1-[(2-phenylethyl)amino]-ethyl}benzenemethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 6.6 g. (0.03 mole) of α-(1-amino-1-methylethyl)benzenemethanol and 4.8 g. (0.03 mole) of phenylacetaldehyde in 75 ml. benzene is refluxed for 1 hour while 0.7 ml. of water separates in a Dean-Stark trap. The infrared absorption spectrum showed absence of the C=O function and the presence of a C=N function at 1650 cm-1. The solvent is removed in vacuo. The residue of the imino derivative was taken up with 60 ml. of methanol and 1.6 g. of KBH4 is added with stirring at 20°-25° C. After 20 hours, the solution is evaporated in vacuo. The residue is taken up with cold water, and the resulting crystalline product (6.8 g., 85% crude yield, m.p. 103°-104° C.) is collected by filtration. Recrystallization from methanol gives pure α-{1-methyl-1-[(2-phenylethyl)amino]-ethyl}benzenemethanol as white crystals, m.p. 105°-106° C.

Workup

  1. customThe infrared absorption spectrum
  2. customThe solvent is removed in vacuo
  3. additionof KBH4 is added
  4. customthe solution is evaporated in vacuo
  5. filtrationthe resulting crystalline product (6.8 g., 85% crude yield, m.p. 103°-104° C.) is collected by filtration
  6. customRecrystallization from methanol

Sources & evidence

ORD record
ord-bd0230f24c134626a721674fb74e837a
Source dataset
uspto-grants-1981_04
Patent number
US04261890

Reaction notes

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