Water → HCID 59322917, compound

HRID 331216Notes

Reaction equation

HRID 331216 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C@H:7]2[N:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]2[C:20]([NH2:25])=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:14][CH2:13]1.[C:26](N1C=CN=C1)(N1C=CN=C1)=[O:27].O>O1CCCC1>[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C@H:7]2[N:12]1[CH2:13][CH2:14][CH:15]([N:18]2[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[NH:25][C:26]2=[O:27])[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 68703619HCID 68703619, compound

Product 1

HCID 59322917HCID 59322917, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-N-[1-(5-Methyl-1,2,3,4-tetrahydronaphthalen-1-yl)piperidin-4-yl]-benzene-1,2-diamine (1.83 g) was dissolved in tetrahydrofuran (100 ml), 1,1′-carbonyldiimidazole (973 mg) was added, and the mixture was stirred at room temperature for 10 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) and crystallized with hexane/ethyl acetate to give the title compound (1.2 g) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)
  6. customcrystallized with hexane/ethyl acetate

Sources & evidence

ORD record
ord-3626f2e37d6d49b0aa074a5bcb74ef9b
Source dataset
uspto-grants-2014_11
Patent number
US08877779B2

Reaction notes

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