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

HRID 356367

반응식

HRID 356367 반응식
B.CSC.[CH3:5][CH:6]([NH:13][C:14](=O)[CH3:15])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>C1COCC1>[CH2:14]([NH:13][CH:6]([CH3:5])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH3:15]

참가 물질

4

반응물 2

HCID 529463N-(Octan-2-yl)acetamideHCID 12423031(Dimethyl sulfide)trihydroboron

생성물 1

HCID 5250531-Heptanamine, 1-methyl, N-ethyl수율 78.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3677ca4cd85944ba851c285dde583129
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834447

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