N,N,N',N',N'',N''-Hexamethylmethanetriamine → HCID 86739947, compound

HRID 745522Notes

Reaction equation

HRID 745522 reaction equation
[C:1]([N:3]1[C@H:12]2[C@@H:7]([CH2:8][C:9](=[O:13])[CH2:10][CH2:11]2)[CH2:6][CH2:5][CH2:4]1)#[N:2].[CH3:14][N:15]([CH:17](N(C)C)N(C)C)[CH3:16]>C1(C)C=CC=CC=1>[C:1]([N:3]1[C@H:12]2[C@@H:7]([CH2:8][C:9](=[O:13])[C:10](=[CH:14][N:15]([CH3:17])[CH3:16])[CH2:11]2)[CH2:6][CH2:5][CH2:4]1)#[N:2]

Participants

4

Reactant 2

HCID 79831N,N,N',N',N'',N''-HexamethylmethanetriamineHCID 13084758HCID 13084758, compound

Product 1

HCID 86739947HCID 86739947, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A reaction mixture was prepared from 4.18 g. of trans-(±)-1-cyano-6-oxodecahydroquinoline, 5.0 g. of tris-dimethylaminomethane and 50 ml. of toluene. The reaction mixture was refluxed under nitrogen temperature for five hours and then was concentrated in vacuo. Five and seventy-six hundredths grams of a crude yellow solid comprising trans-(±)-1-cyano-6-oxo-7-dimethylaminomethylenedecahydroquinoline were obtained. This crude product was mixed with 2.25 g. of guanidine carbonate in 100 ml. of anhydrous methanol. This reaction mixture was heated to reflux under nitrogen overnight, and was then concentrated in vacuo. The resulting solid residue was triturated with hot methanol and filtered. The filter cake was washed twice with methanol and once with ether. A yield of 4.11 g. (78%) of trans-(±)-2-amino-6-cyano-5,5a,6,7,8,9,9a,10-octahydropyrimido[4,5-g]quinoline were obtained having the following physical characteristics. Mass spectrum, molecular ion at 229; infrared spectrum peaks at 3307.18, 3157.70, 2202.87, 1660.83, 1599.10, 1564.38, 1486.26.

Workup

  1. customA reaction mixture was prepared from 4.18 g
  2. temperatureThe reaction mixture was refluxed under nitrogen temperature for five hours
  3. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-aeb3b32bde2e49759296b2c5c22e32a9
Source dataset
uspto-grants-1986_07
Patent number
US04599339

Reaction notes

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