Acetic Acid → N-heptyl-N-[(1-methylindol-2-yl)methyl]amine

HRID 1725235

반응식

HRID 1725235 반응식
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH:11]=O.[CH2:13]([NH2:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C.O>[CH2:13]([NH:20][CH2:11][C:3]1[N:2]([CH3:1])[C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 81271-HeptanamineHCID 2671641-Methylindole-2-carboxaldehydeHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 68855834N-heptyl-N-[(1-methylindol-2-yl)methyl]amine수율 61%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a solution of 1-methylindole-2-carbaldehyde (1.59 g, 10.0 mmol) and heptylamine (1.49 mL, 10.0 mmol) in ethanol (50 mL) were added acetic acid (2.3 mL, 40 mmol) and sodium cyanoborohydride (0.75 g, 12.0 mmol) and the reaction mixture was stirred at room temperature overnight. Water (5 mL) was added and the mixture was concentrated in vacuo. The residue was taken up in ethyl acetate (75 mL) and aqueous 1 M KOH (75 mL) and the phases were separated. The aqueous layer was extracted with ethyl acetate (2×75 mL) and the combined organic phase was washed with brine (75 mL), dried over Na2SO4, and concentrated in vacuo. Purification on a column of silica gel (130 g) with ethyl acetate (17-33% gradient) in heptane as the eluent yielded 1.57 g (61%) of a yellow oil, which solidified upon standing.

후처리

  1. concentrationthe mixture was concentrated in vacuo
  2. customaqueous 1 M KOH (75 mL) and the phases were separated
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×75 mL)
  4. washthe combined organic phase was washed with brine (75 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customPurification on a column of silica gel (130 g) with ethyl acetate (17-33% gradient) in heptane as the eluent

출처 및 근거

ORD 기록
ord-184d1136bece4a75ba16d8502b7d67e2
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07488844B2

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