N-(Octan-2-yl)acetamide → 1-Heptanamine, 1-methyl, N-ethyl

A 2M THF solution of borane-dimethylsulfide (31.5 mL, 63 mmol) was added dropwise to an ice water-cooled solution of N-(1-methylhept-1-yl)acetamide (5.13 g, 30 mmol) in THF (60 mL). The resulting solution was stirred at RT for 1 h, then was refluxed overnight. With ice-water cooling, the excess borane-dimethylsulfide was quenched by the dropwise addition of methanol (10 mL), and the mixture was allowed to stand at RT overnight. The amine hydrochloride could not be precipitated with the addition of HCl gas, so the amine hydrochloride was extracted into dilute HCl. The acidic aq solution was extracted with ether, then made basic and extracted with ethyl acetate. The ethyl acetate solution was dried (MgSO4) and concentrated to afford 3.70 g of impure N-ethyl-N-(1-methylhept-1-yl)amine as an amber oil.

1. temperaturewas refluxed overnight
2. customWith ice-water cooling, the excess borane-dimethylsulfide was quenched by the dropwise addition of methanol (10 mL)
3. waitto stand at RT overnight
4. customThe amine hydrochloride could not be precipitated with the addition of HCl gas, so the amine hydrochloride
5. extractionwas extracted into dilute HCl
6. extractionThe acidic aq solution was extracted with ether
7. extractionextracted with ethyl acetate
8. dry with materialThe ethyl acetate solution was dried (MgSO4)
9. concentrationconcentrated

ORD record

ord-d0129fb0a93a4fb1aa9814e9459e8719

Source dataset

uspto-grants-1998_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05705513