Sodium hydride → 2-Phenyl-2,3,4,5-tetrahydro-[6H]-1,5-benzoxazocine

HRID 1248791ノート

反応式

HRID 1248791 の反応式
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][NH:9][CH2:10][CH2:11][CH:12]([OH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Na+]>CS(C)=O>[C:13]1([CH:12]2[CH2:11][CH2:10][NH:9][CH2:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[O:19]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

4

反応物 2

HCID 24758Sodium hydrideHCID 12951841N-(2-Fluorophenylmethyl)-3-hydroxy-3-phenylpropylamine

生成物 1

HCID 129518422-Phenyl-2,3,4,5-tetrahydro-[6H]-1,5-benzoxazocine収率 40.9%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
50 °C

実験手順

A mixture of N-(2-fluorophenylmethyl)-3-hydroxy-3-phenylpropylamine (4.5 g, 17 mM), 50% sodium hydride dispersion (870 mg, 17 mM) and dimethylsulphoxide (200 ml) was stirred for 24 hours at 50° C. under argon. The mixture was cooled to ambient temperature, poured onto water (700 ml) and extracted with ether (3×200 ml). The combined ether layers were extracted with 1N hydrochloric acid (3×50 ml), the acid layer basified and extracted with ether (2×200 ml). The organic phase was dried and the solvent removed under reduced pressure. Recrystallisation from cyclohexane gave the title compound (1.7 g) m.p. 73°-4° C.

後処理

  1. temperatureThe mixture was cooled to ambient temperature
  2. additionpoured onto water (700 ml)
  3. extractionextracted with ether (3×200 ml)
  4. extractionThe combined ether layers were extracted with 1N hydrochloric acid (3×50 ml)
  5. extractionextracted with ether (2×200 ml)
  6. customThe organic phase was dried
  7. customthe solvent removed under reduced pressure
  8. customRecrystallisation from cyclohexane

出典と根拠

ORDレコード
ord-5fbd87f1ef0a42cea6deceb1ade6cec3
出典データセット
uspto-grants-1986_12
特許番号
US04626522

反応ノート

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