Tetrahydrofuran → N-[(2-bromophenyl)methyl]cyclopropanamine

HRID 1631153ノート

反応式

HRID 1631153 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.O1CCCC1.[CH:15]1([NH2:18])[CH2:17][CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.O.C(O)(=O)C>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH:18][CH:15]1[CH2:17][CH2:16]1

参加物

8

反応物 4

HCID 8028TetrahydrofuranHCID 69828CyclopropylamineHCID 811292-BromobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 20120601N-[(2-bromophenyl)methyl]cyclopropanamine

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 176Acetic Acid溶媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

1 ml of 2-bromobenzaldehyde are dissolved in 20 ml of 1,2-dichloroethane and ml of tetrahydrofuran. 799 μl of cyclopropylamine and 643 μl of glacial acetic acid are added, and the mixture is stirred at 60° C. for 6 h. After cooling to 25° C., 5.3 g of sodium triacetoxyborohydride are added and stirred at 25° C. for a further 12 h. The mixture is poured into water, extracted three times with dichloromethane, and the combined organic phases are dried over sodium sulfate. After filtration, the filtrate is evaporated to dryness and purified by chromatography (reversed phase HPLC).

後処理

  1. temperatureAfter cooling to 25° C.
  2. stirringstirred at 25° C. for a further 12 h
  3. extractionextracted three times with dichloromethane
  4. dry with materialthe combined organic phases are dried over sodium sulfate
  5. filtrationAfter filtration
  6. customthe filtrate is evaporated to dryness
  7. custompurified by chromatography (reversed phase HPLC)

出典と根拠

ORDレコード
ord-1d3450ae3bd44f089cabb5d6c30401eb
出典データセット
uspto-grants-2014_07
特許番号
US08791129B2

反応ノート

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