Benzylamine → 1-Benzyl-2,5-dihydropyrrole

HRID 1018048

反応式

HRID 1018048 の反応式
C(O)/C=C\CO.[CH2:7]([N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[CH3:8].CS(Cl)(=O)=O.C(N)[C:20]1[CH:25]=[CH:24]C=[CH:22][CH:21]=1>C(OCC)(=O)C>[CH2:7]([N:9]1[CH2:12][CH:13]=[CH:11][CH2:10]1)[C:8]1[CH:24]=[CH:25][CH:20]=[CH:21][CH:22]=1

参加物

6

反応物 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 6437902-Butene-1,4-diol, (2Z)-

生成物 1

HCID 5615061-Benzyl-2,5-dihydropyrrole収率 82%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
5 °C

実験手順

To a solution containing 35.4 g (0.4 mol) of cis-2-butene-1,4-diol, 83.8 g (0.8 mol) of triethylamine, and 416.6 g of ethyl acetate in a round flask reactor, methanesulfonyl chloride was added dropwise with stirring for 30 min. at about 5° C. using an ice-bath. After addition, the mixture was allowed to react with stirring for 2 hours at room temperature. To the mixture, 171.7 g (1.6 mol) of benzylamine was added continuously dropwise with stirring for 30 min. at ambient temperature. After 2 hours of stirring, the crystallized solid was removed by filtration; 42.0 g of 35% HCl (aq) was added to the filtrate, and then excess benzylamine hydrochloride was removed by filtration or extraction. After the solvent was evaporated under reduced pressure, 52.2 g of 1-benzyl-3-pyrroline (yield 82.0%) was obtained.

後処理

  1. additionAfter addition
  2. customto react
  3. stirringwith stirring for 2 hours at room temperature
  4. stirringwith stirring for 30 min. at ambient temperature
  5. stirringAfter 2 hours of stirring
  6. customthe crystallized solid was removed by filtration
  7. addition42.0 g of 35% HCl (aq) was added to the filtrate
  8. customexcess benzylamine hydrochloride was removed by filtration or extraction
  9. customAfter the solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-70e69831df4f44189c995d7bf82f4324
出典データセット
uspto-grants-2002_11
特許番号
US06479668B1

関連ノート

読み込み中…