Sodium Hydroxide → HCID 19768383, compound

HRID 1590956Notes

Reaction equation

[CH2:1]([NH:5][CH:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[NH:9][C:8]([CH3:15])([CH3:14])[CH2:7]1)[CH2:2][CH2:3][CH3:4].Cl[C:17]1[N:22]=[C:21](Cl)[N:20]=[C:19]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[N:18]=1.[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[CH3:12][C:10]1([CH3:13])[CH2:11][CH:6]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:17]2[N:22]=[C:21]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH:6]3[CH2:7][C:8]([CH3:14])([CH3:15])[NH:9][C:10]([CH3:13])([CH3:12])[CH2:11]3)[N:20]=[C:19]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[N:18]=2)[CH2:7][C:8]([CH3:14])([CH3:15])[NH:9]1

Participants

Conditions

Temperature: 70 °C

Procedure

4-n-Butylamino-2,2,6,6-tetramethylpiperidine (31.7 g, 149 mmol) is added over 15 minutes to a suspension of 15.0 g (67.8 mmol) of the 2,4-dichloro-6-diethylamino-1,3,5-triazine, 150 ml of xylene, and 7.0 g of powdered sodium hydroxide that had been heated to 70° C. The reaction mixture is heated at reflux for 23 hours. Sodium chloride is removed by filtration, and the filtrate is concentrated to a viscous oil. Further concentration of the oil by Kugelrohr distillation (140°-50° C., 0.05 mm) yields a residue which is crystallized from methanol-water to afford 25.8 g (66% yield) of 2,4-bis[N-(2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-6-diethylamino-1,3,5-triazine, m.p. 74°-76° C.

Workup

temperatureThe reaction mixture is heated
temperatureat reflux for 23 hours
customSodium chloride is removed by filtration
concentrationthe filtrate is concentrated to a viscous oil
distillationFurther concentration of the oil by Kugelrohr distillation (140°-50° C., 0.05 mm)
customyields a residue which
customis crystallized from methanol-water

Sources & evidence

ORD record: ord-ad3d249c8f154474867d4890da36a4ec
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05204473

Reaction notes

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