Water → HCID 18440732, compound

HRID 457756Notes

Reaction equation

HRID 457756 reaction equation
Br[CH2:2][C:3]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7]C)=O.[NH2:16][CH2:17][CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1.C(N(CC)CC)C.O>CN(C=O)C.ClCCl>[N+:13]([C:12]1[CH:11]=[CH:10][CH:9]=[C:4]2[C:3]=1[CH2:2][N:16]([CH2:17][CH2:18][CH:19]1[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH2:24]1)[C:5]2=[O:7])([O-:15])=[O:14]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 1487795Methyl 2-(bromomethyl)-3-nitrobenzoateHCID 1514258tert-Butyl 4-(2-aminoethyl)piperidine-1-carboxylate

Product 1

HCID 18440732HCID 18440732, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

2.7 g (9.81 mmol) of methyl 2-(bromomethyl)-3-nitrobenzoate (J. Org. Chem., 1999, 9731–9734) and 2.25 g (9.81 mmol) of tert-butyl 4-(2-aminoethyl)-1-piperidinecarboxylate (J. Med. Chem., 1997, 1779–1788) are dissolved in 45 ml of absolute DMF, 2.05 ml of triethylamine are added and the mixture is stirred at 70° C. for 2 h. After cooling, water is added to the reaction mixture. The organic phase is taken up in dichloromethane, dried over magnesium sulfate and concentrated. The crude product is purified by chromatography on silica gel.

Workup

  1. temperatureAfter cooling
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe crude product is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-ec1c44e02dac4b359cb343b61a115b09
Source dataset
uspto-grants-2007_03
Patent number
US07189738B2

Reaction notes

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