Water → HCID 18616321, compound

HRID 1263473Notes

Reaction equation

HRID 1263473 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.CC[N:13]=C=NCCCN(C)C.[CH2:22]([CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH2:22]([CH:29]1[CH2:34][CH2:33][N:32]([C:4]2[CH:3]=[C:2]([NH2:1])[CH:10]=[CH:9][C:5]=2[C:6]([NH2:13])=[O:8])[CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 9784-Aminobenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 317384-Benzylpiperidine

Product 1

HCID 18616321HCID 18616321, compoundYield 51.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

4-Aminobenzoic acid (1.61g, 10 mM) was reacted with EDAC (1.92g, 10 mM) in 40 mL dry DMF for 15 minutes. 4-Benzylpiperidine (1.75g, 10 mM) was added followed by DMAP (20 mg, catalyst) and the reaction mixture was stirred for 20 h. The mixture was poured into water and extracted with methylene chloride (3×100 mL). The combined extract was washed with dilute hydrochloric acid, saturated sodium bicarbonate and water and dried over MgSO4. After evaporation of the solvent, the residue was chromatographed with methylene chloride-methanol (0 to 2% methanol, gradient) to yield 1.60 g (50%) of the title compound after recrystallization from ether-Hexane. 1H NMR (CDCl3): δ 7.40-7.10 (m, 7H), 6.70 (d, 2H), 3.95-3.90 (broad m, 2H), 2.85-2.75 (broad m, 2H), 2.6 (d, 2H), 1.85-1.80 (m, 1H), 2.75-2.65 (broad m, 2H), 1.15-1.05 (broad m, 2H). MS (ESI) m/e 294 (M+).

Workup

  1. extractionextracted with methylene chloride (3×100 mL)
  2. extractionThe combined extract
  3. washwas washed with dilute hydrochloric acid, saturated sodium bicarbonate and water
  4. dry with materialdried over MgSO4
  5. customAfter evaporation of the solvent
  6. customthe residue was chromatographed with methylene chloride-methanol (0 to 2% methanol, gradient)

Sources & evidence

ORD record
ord-7a418637f1954e9094a10593d1a7ff14
Source dataset
uspto-grants-2003_04
Patent number
US06541477B2

Reaction notes

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