1-Bromooctane → HCID 20322535, compound

HRID 840003Notes

Reaction equation

[K].[CH2:2]([C:4]1([CH3:20])[NH:15][C:14]([CH2:17][CH3:18])([CH3:16])[CH2:13][C:6]2([NH:10][C:9](=[O:11])[NH:8][C:7]2=[O:12])[CH:5]1[CH3:19])[CH3:3].[CH2:21](Br)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>CN(C)C=O>[CH2:2]([C:4]1([CH3:20])[NH:15][C:14]([CH2:17][CH3:18])([CH3:16])[CH2:13][C:6]2([NH:10][C:9](=[O:11])[N:8]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:7]2=[O:12])[CH:5]1[CH3:19])[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

To 70 ml of dimethylformamide were added 8 g of the potassium salt of 7,9-diethyl-6,7,9-trimethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione (Compound 1) and 5.2 g of octyl bromide; the mixture was heated, with stirring, at 60° C for 2 hours. The reaction mixture was then concentrated by evaporation under reduced pressure, and benzene was added to the residue. The resulting benzene solution was washed with water and then dried over magnesium sulphate. After removing the benzene, the resulting oily product was first purified by column chromatography on silica gel (eluent: benzene containing 5% of triethylamine) and then by recrystallization from hexane, giving 3.0 g of Compound 5, mp 65° - 67° C.

Workup

temperaturethe mixture was heated
concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure, and benzene
additionwas added to the residue
washThe resulting benzene solution was washed with water
dry with materialdried over magnesium sulphate
customAfter removing the benzene
customthe resulting oily product was first purified by column chromatography on silica gel (eluent: benzene containing 5% of triethylamine)
customby recrystallization from hexane

Sources & evidence

ORD record: ord-a113adb3b1af40ceb38cfcd397f3a084
Source dataset: uspto-grants-1978_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04097587

Reaction notes

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