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

HRID 2402219Notes

Reaction equation

HRID 2402219 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-22ecec8ea070423fb1727b0a48db39ec
Source dataset
uspto-grants-2014_08
Patent number
US08796319B2

Reaction notes

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