O-Phenylenediamine → HCID 68704972, compound

HRID 331227Notes

Reaction equation

HRID 331227 reaction equation
[CH:1]1([N:13]2[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][CH:3]3[CH2:2]1.[C:20]1([NH2:27])[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH2:26].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>ClC(Cl)C.O.C(O)(=O)C>[CH:1]1([N:13]2[CH2:18][CH2:17][CH:16]([NH:26][C:21]3[C:20]([NH2:27])=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:15][CH2:14]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][CH:3]3[CH2:2]1

Participants

8

Reactant 4

HCID 7243O-PhenylenediamineHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 687066711-(1,2,2a,3,4,5-Hexahydroacenaphthylen-1-yl)piperidin-4-one

Product 1

HCID 68704972HCID 68704972, compoundYield 85.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a cooled (0° C.) solution of 1-(1,2,2a,3,4,5-hexahydroacenaphthylen-1-yl)piperidin-4-one (1.00 g, 3.92 mmol) and 1,2-phenylenediamine (642 mg) in dichloroethane (30 ml) were added sodium triacetoxyborohydride (1.99 g) and acetic acid (0.509 ml), and the mixture was stirred at room temperature for 19 hr. The reaction mixture was poured into water, and the mixture was neutralized with potassium carbonate, and extracted with chloroform. The extract was washed with water and saturated brine, dried over sodium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (chloroform/methanol) to give N-[1-(1,2,2a,3,4,5-hexahydroacenaphthylen-1-yl)piperidin-4-yl]-benzene-1,2-diamine (1.16 g) as an oil.

Workup

  1. extractionextracted with chloroform
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-c4558bebad384ff8a7c6d7786f699d6c
Source dataset
uspto-grants-2014_11
Patent number
US08877779B2

Reaction notes

Loading…