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Ammonia → HCID 67253556、化合物

HRID 401854
ノート
印刷プレビュー

反応式

HRID 401854 の反応式
N.Br.[CH2:3]([NH:6][C@@H:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH:8]1[Br:16])[CH:4]=[CH2:5].Br.[CH2:18]([NH:21][C@H:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]([Br:31])[CH2:23]1)[CH:19]=[CH2:20].C#CCN[C@H]1C2C=CC=CC=2CC1>Br.O>[CH2:3]([NH:6][C@@H:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH:8]1[Br:16])[CH:4]=[CH2:5].[CH2:18]([NH:21][C@H:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]([Br:31])[CH2:23]1)[CH:19]=[CH2:20]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 222AmmoniaHCID 3052776RasagilineHCID 67254977HCID 67254977、化合物HCID 67255071HCID 67255071、化合物

生成物 2

HCID 67253556HCID 67253556、化合物収率 15%HCID 67254701HCID 67254701、化合物収率 15%

試薬・触媒・溶媒 2

HCID 260Hydrogen Bromide溶媒
HCID 962Water溶媒

実験手順

(R)-Rasagiline base pure (30 g) was dissolved in HBr (250 ml) and the solution was heated to reflux for 36 h. After the completion of reaction the mixture was cooled, diluted with water (500 ml) and slowly the solution was basified using aqueous ammonia solution. The mixture was extracted with methyl tertiary butyl ether (MTBE). The separated MTBE layer was evaporated to get a dark brown oil which exhibited 3 spots on TLC, two of which were of the desired compounds i.e., N-2-Propene-1-yl-2-bromo-(R)-aminoindan hydrobromide (Impurity A) and N-2-Propene-1-yl-3-bromo-(R)-aminoindan hydrobromide (Impurity B). The third spot had same Rf as that of the starting material i.e., the unreacted Rasagiline base. The products formed were separated by column chromatography (silica gel) using hexane-ethyl acetate mixture (75:25) as mobile phase to give pure N-2-Propene-1-yl-2-bromo-(R)-aminoindan (15% overall yield) and N-2-Propene-1-yl-3-bromo-(R)-aminoindan (15% overall yield).

後処理

  1. temperaturethe solution was heated
  2. temperatureto reflux for 36 h
  3. customAfter the completion of reaction the mixture
  4. temperaturewas cooled
  5. extractionThe mixture was extracted with methyl tertiary butyl ether (MTBE)
  6. customThe separated MTBE layer was evaporated
  7. customto get a dark brown oil which
  8. customThe products formed
  9. customwere separated by column chromatography (silica gel)

出典と根拠

ORDレコード
ord-6e3fa063a1b74632b14d706e76fa6896
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08741962B2

反応ノート

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