Dibutylamine → HCID 19928729, compound

HRID 1885210Notes

Reaction equation

C([Li])CCC.[CH2:6]([NH:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7][CH2:8][CH3:9].[O:15]1[C:19]([CH3:26])([CH2:20][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[CH:16]1[CH2:17][OH:18]>O1CCCC1>[CH2:6]([N:10]([CH2:11][CH2:12][CH2:13][CH3:14])[CH:16]([C:19]([CH3:26])([OH:15])[CH2:20][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:17][OH:18])[CH2:7][CH2:8][CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

Under nitrogen atmosphere, 65 ml of n-butyllithium (1.6M in hexane) was added dropwise to a solution of 12.9 g of di-n-butylamine in 30 ml of tetrahydrofuran at -78° C. and after completion of addition, the mixture was stirred at 0° C. for 30 minutes. To this solution was added a solution of 8.6 g of 2,3-epoxy-3,7-dimethyl-1-octanol in 20 ml of tetrahydrofuran slowly in portions at 0° C. The mixture was then stirred at room temperature for 2 hours, after which it was poured into ice-water and extracted with diethyl ether. The extract was washed with water and after drying over anhydrous magnesium sulfate, the solvent was distilled off. The residue was further distilled under reduced pressure to give 12 g of 2-(dibutylamino)-3,7-dimethyl-1,3-octanediol [Compound (59)]. Yield 80%.

Workup

additionafter completion of addition
stirringThe mixture was then stirred at room temperature for 2 hours
extractionextracted with diethyl ether
washThe extract was washed with water
dry with materialafter drying over anhydrous magnesium sulfate
distillationthe solvent was distilled off
distillationThe residue was further distilled under reduced pressure

Sources & evidence

ORD record: ord-b8cd5fd73d1145a1a0aa13cf200b9a89
Source dataset: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05143921

Reaction notes

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