Sulfuric Acid → 2-(4-Chlorophenyl)-2-(4-iodophenyl)morpholine

HRID 45547ノート

反応式

HRID 45547 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:20]=[CH:19][C:18]([I:21])=[CH:17][CH:16]=2)([OH:14])[CH2:9][NH:10][CH2:11][CH2:12]O)=[CH:4][CH:3]=1.OS(O)(=O)=O>C(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:15]3[CH:20]=[CH:19][C:18]([I:21])=[CH:17][CH:16]=3)[O:14][CH2:12][CH2:11][NH:10][CH2:9]2)=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 1118Sulfuric Acid2 回HCID 593319671-(4-Chloro-phenyl)-2-(2-hydroxy-ethylamino)-1-(4-iodo-phenyl)-ethanol

生成物 1

HCID 593319352-(4-Chlorophenyl)-2-(4-iodophenyl)morpholine収率 43.2%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 1-(4-chloro-phenyl)-2-(2-hydroxy-ethylamino)-1-(4-iodo-phenyl)-ethanol (701 mg, 1.68 mmol) in DCM (10 mL) was treated with concentrated H2SO4 (0.1 mL, 1.9 mmol). After 20 hours, another portion of H2SO4 (1.0 mL, 19 mmol) was added and the mixture stirred for a further 2 hours. The mixture was diluted with ethyl acetate and washed with saturated potassium carbonate and brine then dried (MgSO4), filtered and concentrated. The residue was purified by column chromatography (SiO2), eluting with 0.5% triethylamine in ethyl acetate to afford the title compound (290 mg, 43%); LCMS (PS-A2) Rt 2.40 min [M+H]+ 400.

後処理

  1. washwashed with saturated potassium carbonate and brine
  2. dry with materialthen dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (SiO2)
  6. washeluting with 0.5% triethylamine in ethyl acetate

出典と根拠

ORDレコード
ord-e8d30b4030b34c8aadd49ee6df2c0b24
出典データセット
uspto-grants-2013_09
特許番号
US08541461B2

反応ノート

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