Sodium hydride → 4-Fluoro-2-nitro-5-(3-piperidin-1-ylpropoxy)phenylamine

HRID 2274394ノート

反応式

HRID 2274394 の反応式
[N:1]1([CH2:7][CH2:8][CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[F:13][C:14]1[C:19](F)=[CH:18][C:17]([NH2:21])=[C:16]([N+:22]([O-:24])=[O:23])[CH:15]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O.O.C(OCC)(=O)C>[F:13][C:14]1[C:19]([O:10][CH2:9][CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:18][C:17]([NH2:21])=[C:16]([N+:22]([O-:24])=[O:23])[CH:15]=1

参加物

8

反応物 4

HCID 24758Sodium hydrideHCID 66032Piperidine-1-propanolHCID 1571514,5-Difluoro-2-nitroanilineHCID 516892Sodium Bicarbonate

生成物 1

HCID 688437124-Fluoro-2-nitro-5-(3-piperidin-1-ylpropoxy)phenylamine

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 1.3 mL of 3-piperidin-1-ylpropan-1-ol in 16 mL of N,N-dimethylformamide (DMF) is cooled to 0° C. with an ice bath. 345 mg of sodium hydride (60% in suspension in oil) are added in small portions. The suspension obtained is added dropwise to a suspension containing 500 mg of 4,5-difluoro-2-nitrophenylamine and 724 mg of sodium bicarbonate in 15 mL of DMF. The reaction medium is stirred for one hour at ambient temperature and then heated for 1 hour at 90° C. The cooled reaction medium is treated with 70 mL of ethyl acetate and 70 mL of distilled water. The aqueous phase is extracted with 70 mL of ethyl acetate. The combined organic phases are washed with 100 mL of distilled water and 100 mL of a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent is concentrated to dryness in a rotary evaporator and the crude is then purified by chromatography on a 50 g silica cartridge, eluent: 100/0 to 80/20 dichloromethane/methanol. 300 mg of 4-fluoro-2-nitro-5-(3-piperidin-1-ylpropoxy)phenylamine are isolated in the form of a yellow oil which crystallizes. Analytical LC/MS: Tr=2.26 min, [M+H]+=298.04 DAD=87%.

後処理

  1. customThe suspension obtained
  2. additionis added dropwise to a suspension
  3. temperatureheated for 1 hour at 90° C
  4. customThe cooled reaction medium
  5. extractionThe aqueous phase is extracted with 70 mL of ethyl acetate
  6. washThe combined organic phases are washed with 100 mL of distilled water and 100 mL of a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe solvent is concentrated to dryness in a rotary evaporator
  9. customthe crude is then purified by chromatography on a 50 g silica cartridge, eluent

出典と根拠

ORDレコード
ord-c478d36d84034e15b212c1cf638a4e2b
出典データセット
uspto-grants-2015_09
特許番号
US09126969B2

反応ノート

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