Diisopropylethylamine → N-(1-methyl-4-piperidyl)-7-nitro-benzo[1,3]dioxole-4-carboxamide

HRID 2234491Notes

Reaction equation

HRID 2234491 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N+:33]([C:36]1[C:41]2[O:42][CH2:43][O:44][C:40]=2[C:39]([C:45](O)=[O:46])=[CH:38][CH:37]=1)([O-:35])=[O:34].C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH3:8][N:5]1[CH2:6][CH2:7][CH:2]([NH:1][C:45]([C:39]2[C:40]3[O:44][CH2:43][O:42][C:41]=3[C:36]([N+:33]([O-:35])=[O:34])=[CH:37][CH:38]=2)=[O:46])[CH2:3][CH2:4]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27375314-Amino-1-methylpiperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 219488047-Nitrobenzo[d][1,3]dioxole-4-carboxylic acid

Product 1

HCID 68682205N-(1-methyl-4-piperidyl)-7-nitro-benzo[1,3]dioxole-4-carboxamideYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Amino-1-methylpiperidine (Fluorochem; 325 mg, 2.84 mmol), HATU (1.09 g, 2.84 mmol) and 7-nitrobenzo[1,3]dioxole-4-carboxylic acid (WO 2003082827; 400 mg, 1.89 mmol) were stirred in DMF (5 mL) and diisopropylethylamine (0.99 ml, 5.68 mmol) added. The mixture was stirred for 2 hours at room temperature. The reaction mixture was loaded on to an SCX column, which was subsequently washed with methanol and eluted with ammonia in methanol. Product containing fractions were concentrated and the solid suspended in methanol and filtered off to yield the title compound as a yellow solid (295 mg, 51%).

Workup

  1. washwas subsequently washed with methanol
  2. washeluted with ammonia in methanol
  3. additionProduct containing fractions
  4. concentrationwere concentrated
  5. filtrationfiltered off

Sources & evidence

ORD record
ord-eaac18c1bee74422bc4730b858d41712
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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