Hydrochloric Acid → 4-phenyl-N-(piperidine-4-yl)quinazolin-2-amine

HRID 406814

反応式

HRID 406814 の反応式
Cl[C:2]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:18][CH:19]1[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]1.Cl>C(O)CCC.O1CCOCC1>[C:12]1([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=[C:2]([NH:18][CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[N:11]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 12682914-Amino-1-Boc-piperidineHCID 31235822-Chloro-4-phenylquinazoline

生成物 1

HCID 441404384-phenyl-N-(piperidine-4-yl)quinazolin-2-amine収率 117.1%

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of 2-chloro-4-phenylquinazoline (1.38 g, 5.75 mmol), and tert-butyl 4-aminopiperidine-1-carboxylate (2.81 g, 14.1 mmol) was heated at reflux in n-butanol (20 mL) for 4 h. After removal of the n-butanol on a rotary evaporator, dichloromethane (100 mL) was added and the suspension was sonicated for 30 min and filtered. The solution was then concentrated on a rotary evaporator to give a brown residue. This residue was purified by column chromatography on silica gel (95:5 hexanes/ethyl acetate) to yield a green oil that was treated with 4M HCl in 1,4-dioxane (100 mL) at 100° C. for 1 h. The solvent was removed on a rotary evaporator to give 4-phenyl-N-(piperidine-4-yl)quinazolin-2-amine (2.05 g, 90%) as a dark yellow solid.

後処理

  1. customAfter removal of the n-butanol
  2. customon a rotary evaporator, dichloromethane (100 mL)
  3. additionwas added
  4. customthe suspension was sonicated for 30 min
  5. filtrationfiltered
  6. concentrationThe solution was then concentrated on a rotary evaporator
  7. customto give a brown residue
  8. customThis residue was purified by column chromatography on silica gel (95:5 hexanes/ethyl acetate)
  9. customto yield a green oil that
  10. customThe solvent was removed on a rotary evaporator

出典と根拠

ORDレコード
ord-5bacfa027ebd4f24938d25582e667203
出典データセット
uspto-grants-2014_06
特許番号
US08754092B2

関連ノート

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