Water → HCID 15218751, compound

HRID 1590958Notes

Reaction equation

[CH2:1]([NH:5][CH:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[N:9]([O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[C:8]([CH3:22])([CH3:21])[CH2:7]1)[CH2:2][CH2:3][CH3:4].[N:23]1[C:30](Cl)=[N:29][C:27](Cl)=[N:26][C:24]=1[Cl:25].[OH-:32].[Na+].O>C1(C)C(C)=CC=CC=1>[Cl:25][C:24]1[N:23]=[C:30]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH:6]2[CH2:7][C:8]([CH3:21])([CH3:22])[N:9]([O:14][CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]3)[C:10]([CH3:13])([CH3:12])[CH2:11]2)[N:29]=[C:27]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH:6]2[CH2:7][C:8]([CH3:21])([CH3:22])[N:9]([O:32][CH:20]3[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]3)[C:10]([CH3:13])([CH3:12])[CH2:11]2)[N:26]=1

Participants

Conditions

Temperature: 42.5 °C

Procedure

A solution of 36.0 g (116 mmol) of 4-n-butylamino-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine in 100 ml of xylene is added over 20 minutes to a mixture of 10.9 g (59.2 mmol) of cyanuric chloride, 10.0 g of 50% aqueous sodium hydroxide, 10 ml of water, and 50 ml of xylene. The reaction temperature increases from 25 to 60° C. during the addition and is then maintained at 65°-70° C. for six hours. The phases are separated, and the organic phase is dried over magnesium sulfate and concentrated. The residue is purified by flash chromatography (39:1 heptane:ethyl acetate) on silica gel to afford 27.7 g (65% yield) of 2-chloro-4,6-bis-[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-1,3,5-triazine, a white glass, m.p. 75°-82° C.

Workup

temperatureis then maintained at 65°-70° C. for six hours
customThe phases are separated
dry with materialthe organic phase is dried over magnesium sulfate
concentrationconcentrated
customThe residue is purified by flash chromatography (39:1 heptane:ethyl acetate) on silica gel

Sources & evidence

ORD record: ord-0e71d8ff284f46ba9d4dca1e3fb31bdf
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05204473

Reaction notes

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