Diisopropylethylamine → 3-isopropoxy-N-(1-methyl-piperidin-4-yl)-4-nitro-benzamide

HRID 1676533

反応式

HRID 1676533 の反応式
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[C:8]([OH:10])=O)([CH3:3])[CH3:2].C(N(C(C)C)C(C)C)C.[NH2:26][CH:27]1[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]1.F[P-](F)(F)(F)(F)F.CN(C(N(C)C)=[N+]1C2C=CC=CC=2[N+]([O-])=N1)C>C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[C:8]([NH:26][CH:27]1[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]1)=[O:10])([CH3:2])[CH3:3]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 6029283-Isopropoxy-4-nitrobenzoic acidHCID 27375314-Amino-1-methylpiperidineHCID 178484289HCID 178484289、化合物

生成物 1

HCID 670764013-isopropoxy-N-(1-methyl-piperidin-4-yl)-4-nitro-benzamide収率 95.7%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 10340Sodium Carbonate溶媒

実験手順

To a mixture of 0.88 g (3.9 mmole) of 3-isopropoxy-4-nitro-benzoic acid, 2.8 mL (16 mmole) of ethyldiisopropyl amine, 0.54 g (4.7 mmole) of 4-amino-1-methyl-piperidine and 18 mL of dimethylformamide was added 1.63 g (4.3 mmole) of 1-[bis(dimethylamino)methylene)-1H-benzotriazolium 3-oxide hexafluorophosphate. The mixture was stirred at room temperature for 2 hours, then diluted with ice water and saturated sodium carbonate. The mixture was extracted with ethyl acetate 3 times. The combined organic layers were washed three times with sodium carbonate, three times with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel chromatography, eluting with dichloromethane-methanol (gradient, 100:0-40:60) gave 1.2 g of 3-isopropoxy-N-(1-methyl-piperidin-4-yl)-4-nitro-benzamide as a yellow solid.

後処理

  1. extractionThe mixture was extracted with ethyl acetate 3 times
  2. washThe combined organic layers were washed three times with sodium carbonate, three times with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel chromatography
  7. washeluting with dichloromethane-methanol (gradient, 100:0-40:60)

出典と根拠

ORDレコード
ord-9a8a08cb7178483b9f4aea6a46c0219a
出典データセット
uspto-grants-2011_08
特許番号
US08003785B2

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