Trifluoroacetic acid → 4-Amino-1-(4-chloropyrimidin-2-yl)-4-methylpiperidine

HRID 1156

反応式

HRID 1156 の反応式
C(OC([NH:8][C:9]1([CH3:22])[CH2:14][CH2:13][N:12]([C:15]2[N:20]=[C:19]([Cl:21])[CH:18]=[CH:17][N:16]=2)[CH2:11][CH2:10]1)=O)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)Cl>[NH2:8][C:9]1([CH3:22])[CH2:14][CH2:13][N:12]([C:15]2[N:20]=[C:19]([Cl:21])[CH:18]=[CH:17][N:16]=2)[CH2:11][CH2:10]1

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 14798Sodium HydroxideHCID 196949254-t-Butoxycarbonylamino-1-(4-chloropyrimidin-2-yl)-4-methylpiperidine

生成物 1

HCID 196949174-Amino-1-(4-chloropyrimidin-2-yl)-4-methylpiperidine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 2.22 g (0.0068 mol) of 4-t-butoxycarbonylamino-1-(4-chloropyrimidin-2-yl)-4-methylpiperidine (step c) in 25 ml of anhydrous methylene chloride is cooled under a nitrogen atmosphere and 5 ml of anisole and 25 ml of trifluoroacetic acid are added slowly. The mixture is stirred for 1 hour at room temperature and 25 ml of a 30% solution of NaOH are added slowly. The reaction medium is extracted with methylene chloride and dried over Na2SO4 and the solvent and the anisole are evaporated off under reduced pressure. The residue is purified by chromatography using CH2Cl2 /MeOH=9/1 as the eluent to give 4-amino-1-(4-chloropyrimidin-2-yl)-4-methylpiperidine as the base, which is treated with maleic acid in an ethanol/isopropyl ether mixture. The maleate obtained in this way is isolated by filtration (m.p. 154°-155° C.).

後処理

  1. extractionThe reaction medium is extracted with methylene chloride
  2. dry with materialdried over Na2SO4
  3. customthe solvent and the anisole are evaporated off under reduced pressure
  4. customThe residue is purified by chromatography

出典と根拠

ORDレコード
ord-564b28fa70ee43db9e87ffa6d6c4d4e6
出典データセット
uspto-grants-1998_03
特許番号
US05723611

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