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

HRID 1416575

反応式

HRID 1416575 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

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 pH 2.2 by the addition of 33% H2SO4. The phases were separated and the organic layer discarded. The pH of the aqueous layer was adjusted to pH 6.0 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).

後処理

  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

出典と根拠

ORDレコード
ord-adfe738f6c334c5db3d7e348c5b0d788
出典データセット
uspto-grants-1999_06
特許番号
US05914349

関連ノート

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