Sulfuric Acid → 2,3-Dihydro-N-benzyl-1H-inden-1-amine

HRID 1417576

반응식

HRID 1417576 반응식
C1(C)C=CC=CC=1.[CH2:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl[CH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18]1.OS(O)(=O)=O>O>[CH2:8]([NH:15][CH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 7504BenzylamineHCID 944651-Chloro-2,3-dihydro-1H-indene

생성물 1

HCID 101307242,3-Dihydro-N-benzyl-1H-inden-1-amine수율 72.5%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

A mixture of 272 ml of toluene and 199.5 g benzylamine was prepared and heated to 90° C. The chlorindan was added dropwise to the mixture over a 30 minute period. The reaction mixture was heated to 115° C for ten hours. The reaction mixture was cooled to ambient temperature and 300 ml of water was added. The resulting heterogeneous mixture was then brought to pH2.2 by the addition of 33% H2SO4. The phases were separated and the organic layer discarded. The pH of the aqueous layer was adjusted to pH6.0 prior to extraction with 300 ml of toluene. A further 100 ml of toluene was then added and the aqueous phase discarded. The toluene was removed under vacuo from the combined organic layer leaving 104.3 g racemic N-benzyl-1-aminoindan base as an oil (72.5% yield).

후처리

  1. customwas prepared
  2. temperatureThe reaction mixture was heated to 115° C for ten hours
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. customThe phases were separated
  5. extractionto extraction with 300 ml of toluene
  6. additionA further 100 ml of toluene was then added
  7. customThe toluene was removed under vacuo from the combined organic layer

출처 및 근거

ORD 기록
ord-55341bde68cb4194a7184fc3c05e3923
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05877221

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