Phosphorus oxychloride → HCID 12988956、化合物

HRID 1483899ノート

反応式

HRID 1483899 の反応式
[CH2:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13]([NH2:15])=O)[CH2:6][CH2:5]1)[CH2:2][CH3:3].O=P(Cl)(Cl)Cl>CN(C=O)C.O>[CH2:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13]#[N:15])[CH2:6][CH2:5]1)[CH2:2][CH3:3]

参加物

5

反応物 2

HCID 24813Phosphorus oxychlorideHCID 129889553-(1-Propyl-4-piperidinyl)benzamide

生成物 1

HCID 12988956HCID 12988956、化合物収率 39.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 3-(1-propyl-piperidin-4-yl)-benzamide (350 mg) and POCl3 (326 μL) in dry DMF (6 ml) was heated at 80° C. for 3 h under an argon atmosphere. Evaporation of the solvent yielded a dark, oily residue, which was dissolved in water. The solution was basified and extracted with CH2Cl2. The combined organic phases were dried (MgSO4), filtered and evaporated. The oily residue was chromathographed on a silica column with MeOH:CH2Cl2 (1:19 (v/v)) as eluent. Collection of the fractions containing pure product and evaporation of the solvent afforded pure 3-(1-Propyl-piperidin-4-yl)-benzonitrile (127 mg). The amine was converted into the fumarate salt and recrystallized from ethanol/diethylether: m.p. 122° C.; MS m/z (relative intensity, 70 eV) 228 (M+, 2), 199 (42), 129 (26), 70 (bp) 56 (53).

後処理

  1. customEvaporation of the solvent
  2. customyielded a dark, oily residue, which
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customCollection of the fractions
  8. additioncontaining pure
  9. customproduct and evaporation of the solvent

出典と根拠

ORDレコード
ord-49ba9050cd564708b6b6bd9655ad06de
出典データセット
uspto-grants-2016_08
特許番号
USRE046117E1

反応ノート

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