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

HRID 1676533

반응식

HRID 1676533 반응식
[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]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 6029283-Isopropoxy-4-nitrobenzoic acidHCID 27375314-Amino-1-methylpiperidineHCID 178484289HCID 178484289, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 10340Sodium Carbonate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9a8a08cb7178483b9f4aea6a46c0219a
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003785B2

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