Methylamine → HCID 15521810, compound

HRID 2304547Notes

Reaction equation

HRID 2304547 reaction equation
[CH2:1]1[CH:10]2[N:5]([CH2:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9]2=O)[CH2:4][CH2:3][CH2:2]1.[CH3:16][NH2:17]>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH3:16][N:17]=[C:9]1[CH:10]2[N:5]([CH2:4][CH2:3][CH2:2][CH2:1]2)[CH2:6][C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]1=2

Participants

5

Reactant 2

HCID 6329MethylamineHCID 13090243HCID 13090243, compound

Product 1

HCID 15521810HCID 15521810, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of the ketone of example 5 (1.10 g, 5.47 mmol) in CH2Cl2 (20 mL) was added to methylamine (5 mL) followed by the addition of TiCl4 (2.74 mmol, 2.74 mL of 1.0 M solution in toluene). The mixture was stirred at room temperature for 10 h. It was filtered through a pad of diatomaceous earth (sold under the brand name CELITE) and rinsed with CH2Cl2. The filtrate was concentrated in vacuo to give a mixture of red solid and oil (1.29 g, 100%) which was directly used for the next step without purification.

Workup

  1. filtrationIt was filtered through a pad of diatomaceous earth (
  2. washrinsed with CH2Cl2
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give
  5. customwas directly used for the next step without purification

Sources & evidence

ORD record
ord-ebcc0a3eea75450cadbba04cc01a98e5
Source dataset
uspto-grants-2002_08
Patent number
US06436954B1

Reaction notes

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