3-Amino-1-propanol → 3-[(Diphenylmethylene)amino]propan-1-ol

HRID 881158Notes

Reaction equation

HRID 881158 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[C:6](=N)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>ClCCl>[C:7]1([C:6](=[N:1][CH2:2][CH2:3][CH2:4][OH:5])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 136809Benzophenone imine

Product 1

HCID 591484383-[(Diphenylmethylene)amino]propan-1-olYield 101.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-amino-1-propanol [Aldrich product #A76400] (2.0 mL, 26 mmol) in dichloromethane (79 mL) was treated with benzophenone imine (4.4 mL, 26 mmol) and stirred at 25° C. for 16 h. The reaction mixture was filtered and the filtrate was concentrated to give the desired product (6.3 g, quantitative) as an oil. This material was used without further purification. LCMS for C16H18NO (M+H)+: m/z=240.2.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7fa9ad6749a943e3be41b90ebc75d50b
Source dataset
uspto-grants-2015_03
Patent number
US08993605B2

Reaction notes

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