Hydrochloric Acid → 1-[2-(4-Aminopiperidin-1-yl)ethyl]-2-oxo-1,2-dihydroquinoline-7-carbonitrile

HRID 656893ノート

反応式

HRID 656893 の反応式
[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:29])[N:10]2[CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([NH:21]C(=O)OC(C)(C)C)[CH2:17][CH2:16]2)=[CH:5][CH:4]=1)#[N:2].Cl.C1(C)C=CC=CC=1>C(Cl)(Cl)Cl.O1CCOCC1>[NH2:21][CH:18]1[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][N:10]2[C:11]3[C:6](=[CH:5][CH:4]=[C:3]([C:1]#[N:2])[CH:12]=3)[CH:7]=[CH:8][C:9]2=[O:29])[CH2:16][CH2:17]1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 60200429tert-butyl 1-(2-(7-cyano-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-ylcarbamate

生成物 1

HCID 602009201-[2-(4-Aminopiperidin-1-yl)ethyl]-2-oxo-1,2-dihydroquinoline-7-carbonitrile収率 99%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 1,1-dimethylethyl {1-[2-(7-cyano-2-oxo-1(2H)-quinolinyl)ethyl]-4-piperidinyl}carbamate (1.1 g, 2.8 mmol) in chloroform (15 ml) was added 4N HCl in 1,4-dioxane (15 ml) and the reaction stirred at rt for 45 mins. Toluene was then added and the solution was evaporated, dissolved in MeOH and treated with Amberlyst A21 basic resin for 30 m until pH of the solution is basic. The resine was filtered off and the solvent removed; the residue was subjected to column chromatography on silica gel eluting with 0-15% 2M ammonia in methanol-DCM to afford the desired compound (0.82 g, 99%).

後処理

  1. customthe solution was evaporated
  2. dissolutiondissolved in MeOH
  3. additiontreated with Amberlyst A21 basic resin for 30 m until pH of the solution
  4. filtrationThe resine was filtered off
  5. customthe solvent removed

出典と根拠

ORDレコード
ord-d4187a76de6a4a5d8b5fa3cfa26cc2a2
出典データセット
uspto-grants-2011_12
特許番号
US08071592B2

反応ノート

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