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-dimethyl-sulfide 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-dimethyl-sulfide 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-8c19c3b780994889a17ca4ba5b6b3086

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05849723