1,2,3,4-Tetrahydroisoquinoline → 2-[4-(4-Butyl-phenyl)-butyl]-5,6,7,8-tetrahydro-isoquinolinium bromide

HRID 84332

반응식

HRID 84332 반응식
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH3:15])=[CH:8][CH:7]=1.[CH2:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][NH:17]1>C(#N)C>[Br-:1].[CH2:12]([C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][N+:17]2[CH:18]=[CH:19][C:20]3[CH2:21][CH2:22][CH2:23][CH2:24][C:25]=3[CH:16]=2)=[CH:7][CH:8]=1)[CH2:13][CH2:14][CH3:15]

참가 물질

4

반응물 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 198479361-(4-Bromo-butyl)-4-butyl-benzene

생성물 1

HCID 247807972-[4-(4-Butyl-phenyl)-butyl]-5,6,7,8-tetrahydro-isoquinolinium bromide수율 72%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

1-(4-Bromo-butyl)-4-butyl-benzene (1 mmol) was added to a solution of tetrahydroisoquinoline (2 mmol) in acetonitrile, and the solution was refluxed for 24 hours. The acetonitrile was removed in vacuum, and the resulting residue was partitioned between ether and water. The aqueous layer was washed extensively with ether until no tetrahydroisoquinoline was left in the aqueous layer. The resulting aqueous solution of the product was extracted with chloroform. The chloroform was removed to afford the product (72%). 1HNMR (300 MHz, CDCl3, ppm), 9.12 (s, 1H), 8.85 (d, J=6.0, 1H), 7.61 (d, J=6.0, 1H), 7.02-7.08 (m, 4H), 4.83 (t, 7.5, 3H), 2.92-2.94 (m, 4H), 2.61 (t, J=7.5, 2H), 2.54 (t, J=7.5, 2H), 1.90-2.04 (m, 2H), 1.80-1.90 (m, 4H), 1.62-1.69 (m, 2H), 1.53-1.62 (m, 2H), 1.29-1.37 (m, 2H), 0.90 (t, J=7.2, 3H). 13CNMR, 157.94, 144.18, 140.82, 140.64. 138.96, 138.37, 128.65, 128.48, 127.99, 61.16, 35.54, 34.99, 34.05, 31.56, 29.92, 27.98, 26.69, 22.74, 21.37, 14.33.

후처리

  1. temperaturethe solution was refluxed for 24 hours
  2. customThe acetonitrile was removed in vacuum
  3. customthe resulting residue was partitioned between ether and water
  4. washThe aqueous layer was washed extensively with ether until no tetrahydroisoquinoline
  5. waitwas left in the aqueous layer
  6. extractionThe resulting aqueous solution of the product was extracted with chloroform
  7. customThe chloroform was removed

출처 및 근거

ORD 기록
ord-aa860c4521af4631b575d56c6aea8109
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846937B2

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