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Hydrochloric Acid → tert-Butyl 4-(5-(trifluoromethyl)pyridin-2-ylamino)piperidine-1-carboxylate

HRID 511100
ノート
印刷プレビュー

反応式

HRID 511100 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][N:17]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.ClCCl.C(OC(=O)C)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][N:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 12682914-Amino-1-Boc-piperidine

生成物 1

HCID 58576452tert-Butyl 4-(5-(trifluoromethyl)pyridin-2-ylamino)piperidine-1-carboxylate収率 55%

試薬・触媒・溶媒 3

HCID 679
Dimethyl Sulfoxide
溶媒
HCID 962Water溶媒
HCID 21226138Dichloromethane ethylacetate溶媒

実験手順

A solution of 4-amino-piperidine-1-carboxylic acid tert-butyl ester (400 mg; 2.0 mmol), 2-chloro-5-trifluoromethyl-pyridine (362 mg; 2.0 mmol) and potassium carbonate (280 mg; 2.0 mmol) in dimethylsulfoxide (3 mL) is heated 10 hours at 120° C. The reaction is then cooled to room temperature, water (20 mL) is added and the pH is set to 4-5 by addition of aq. 1N hydrochloric acid. The aqueous layer is then extracted with dichloromethane (4×20 mL), the combined organic layers are dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue obtained is finally purified by column chromatography on silica gel (dichloromethane and then dichloromethane:ethylacetate 8:1) to afford the desired product (380 mg; 1.10 mmol).

後処理

  1. extractionThe aqueous layer is then extracted with dichloromethane (4×20 mL)
  2. dry with materialthe combined organic layers are dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customis finally purified by column chromatography on silica gel (dichloromethane

出典と根拠

ORDレコード
ord-7b3ce21819e34585acb31acd34a13938
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09096524B2

反応ノート

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