Diisopropylamine → (1,1'-Biphenyl)-2-carboxamide

HRID 1989872

反応式

HRID 1989872 の反応式
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:2]([C:7](O)=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.S(Cl)(Cl)=O.C1(C[N:27]2CCC(C3C=CC(N)=CC=3)CC2)C=CC=CC=1.CC(NC(C)C)C>C(Cl)Cl.CN(C=O)C>[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:2]([C:7]([NH2:27])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

7

反応物 4

HCID 7912DiisopropylamineHCID 24386Thionyl ChlorideHCID 70357o-Phenylbenzoic acidHCID 224993964-[1-(Phenylmethyl)-4-piperidinyl]-benzenamine

生成物 1

HCID 83254(1,1'-Biphenyl)-2-carboxamide収率 253.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

2-Biphenylcarboxylic acid (0.25 mol) was dissolved in DCM (500 ml) and DMF (0.5 ml). Thionyl chloride (0.51 mol) was added dropwise. The mixture was stirred and refluxed for 1 hour under nitrogen flow. The solvent was evaporated. DCM (500 ml) was added twice. The solvent was evaporated twice. The residue was dissolved in DCM (200 ml) and then added dropwise at 0° C. to a mixture of 4-[1-(phenylmethyl)-4-piperidinyl]-benzenamine (0.25 mol) and N-(1-methylethyl)-2-propanamine (0.75 mol) in DCM (800 ml). The mixture was brought to room temperature and then stirred at room temperature overnight under nitrogen flow. The mixture was washed three times with water (800 ml). The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 125 g of [1,1′-biphenyl]-2-carboxamide, N-[4-[1-(phenylmethyl)-4-piperidinyl]phenyl]-(intermediate 39).

後処理

  1. temperaturerefluxed for 1 hour under nitrogen flow
  2. customThe solvent was evaporated
  3. additionDCM (500 ml) was added twice
  4. customThe solvent was evaporated twice
  5. dissolutionThe residue was dissolved in DCM (200 ml)
  6. customwas brought to room temperature
  7. stirringstirred at room temperature overnight under nitrogen flow
  8. washThe mixture was washed three times with water (800 ml)
  9. customThe organic layer was separated
  10. customdried
  11. filtrationfiltered
  12. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-e652dd9fed5846eaa8cce00d70d967af
出典データセット
uspto-grants-2010_01
特許番号
US07642378B2

関連ノート

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