Acryloyl chloride → N-(11-hydroxy-undecyl)-N-methyl acrylamide

HRID 1052939Notes

Reaction equation

[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]O.[OH-:15].[Na+].[C:17](Cl)(=[O:20])[CH:18]=[CH2:19]>ClCCl.O>[OH:15][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[C:17](=[O:20])[CH:18]=[CH2:19]

Participants

Conditions

Temperature: -5 °C

Procedure

11-methylamino undecan-1-ol (10.07 g, 50.0 mmol) was dissolved in dichloromethane (30 ml). A solution of sodium hydroxide (2.40 g, 60.0 mmol) in water (30 ml) was added. The mixture was cooled to −5° C. and a solution of acrylic acid chloride (4.75 g, 52.5 mmol) and BHT (10 mg) in dichloromethane (30 ml) was added dropwise. Once the addition had ended the reaction mixture was stirred for 2 h at −5° C. and for a further 16 h at RT. Organic and aqueous phases were separated. The aqueous phase was saturated with NaCl and extracted with dichloromethane (2×50 ml). The combined organic phases were dried over Na2SO4, filtered and concentrated on the rotary evaporator. The crude product was purified by means of column chromatography (SiO2/ethyl acetate). 10.38 g (40.6 mmol; 81% yield) of a yellowish liquid was obtained.

Workup

additionOnce the addition
customOrganic and aqueous phases were separated
extractionextracted with dichloromethane (2×50 ml)
dry with materialThe combined organic phases were dried over Na2SO4
filtrationfiltered
concentrationconcentrated on the rotary evaporator
customThe crude product was purified by means of column chromatography (SiO2/ethyl acetate)
custom10.38 g (40.6 mmol; 81% yield) of a yellowish liquid was obtained

Sources & evidence

ORD record: ord-9f94f9495c884a83801c244482a3d598
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09393181B2

Reaction notes

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