Methylamine → HCID 21541758, compound

HRID 1076071Notes

Reaction equation

HRID 1076071 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:17][NH2:18]>[Ti](Cl)(Cl)(Cl)Cl.C1C=CC=CC=1>[CH3:17][N:18]=[C:6]1[C:5]2[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=2[CH:10]=[CH:9][C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]1=2

Participants

5

Reactant 2

HCID 6329MethylamineHCID 166795H-Dibenzo[a,d]cyclohepten-5-one

Product 1

HCID 21541758HCID 21541758, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 241BenzeneSolvent

Procedure

Using the procedure following Example 1, a mixture of 100 g 0f 5H-dibenzo[a,d]-cyclohepten-5-one, 98 g of methylamine and 1000 ml of benzene is treated with 53 g of titanium tetrachloride. The mixture is worked up after stirring at room temperature for 6 days. Short-path distillation of the crude product at 120° bath temperature and 0.1 micron pressure gives 101.2 g (95% yield) of N-methyl-5H-dibenzo[a,d]cyclohepten-5-imine as a viscous oil that solidifies slowly on standing. Nmr spectrum (in CDCl3): multiplet at τ 2.3-2.9 (8H) and singlets at 3.2 (2H) and 6.7 (3H).

Workup

  1. distillationShort-path distillation of the crude product at 120° bath temperature and 0.1 micron pressure

Sources & evidence

ORD record
ord-85bdfb3b77024e8db62d8a77a2fe9bf3
Source dataset
uspto-grants-1976_05
Patent number
US03954865

Reaction notes

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