Cyclobutanone → N-cyclobutylidene-1-(4-methoxyphenyl)methanamine

HRID 2362712Notes

Reaction equation

HRID 2362712 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.[C:11]1(=O)[CH2:14][CH2:13][CH2:12]1>C(OCC)C>[C:11]1(=[N:10][CH2:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 14496CyclobutanoneHCID 754524-Methoxybenzylamine

Product 1

HCID 58513739N-cyclobutylidene-1-(4-methoxyphenyl)methanamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of (4-methoxyphenyl)methanamine (9.26 mL, 71.3 mmol) and cyclobutanone (5.35 mL, 71.3 mmol) in anhydrous ethyl ether (70 mL) was treated with activated 4 angstrom molecular sieves (2.5 g). The mixture was stirred vigorously for 16 hours at ambient temperature. The reaction mixture was filtered, and the sieves were washed with ethyl ether. The filtrate was concentrated under reduced pressure with no heat. The title compound was stored under nitrogen and used without further purification. MS DCI(+) m/z 190.3 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe sieves were washed with ethyl ether
  3. concentrationThe filtrate was concentrated under reduced pressure with no heat
  4. customused without further purification

Sources & evidence

ORD record
ord-f1d9da33223342feba165a1c3aef4ef6
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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