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

HRID 1676533

Reaction equation

HRID 1676533 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 10340Sodium CarbonateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-9a8a08cb7178483b9f4aea6a46c0219a
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Linked notes

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