O-Phenylenediamine → HCID 68703619, compound

HRID 331215Notes

Reaction equation

HRID 331215 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][C:15](=O)[CH2:14][CH2:13]1.[C:19]1([NH2:26])[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH2:25].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClC(Cl)C.C(O)(=O)C>[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:25][C:20]2[C:19]([NH2:26])=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 7243O-PhenylenediamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 68704558HCID 68704558, compound

Product 1

HCID 68703619HCID 68703619, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 63651,1-DichloroethaneSolvent

Procedure

(R)-1-(5-Methyl-1,2,3,4-tetrahydronaphthalen-1-yl)piperidin-4-one (1.84 g) was dissolved in dichloroethane (55 ml), and 1,2-phenylenediamine (1.23 g) was added. To the solution were added sodium triacetoxyborohydride (3.61 g) and acetic acid (0.97 ml). The mixture was stirred at room temperature for 24 hr, alkalified with saturated sodium hydrogen carbonate, and extracted with chloroform. 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) to give (R)-N-[1-(5-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)piperidin-4-yl]-benzene-1,2-diamine (1.83 g) as a pale-brown solid.

Workup

  1. extractionextracted with chloroform
  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)

Sources & evidence

ORD record
ord-253f71e86bbe4cf985f3ef81a564d46c
Source dataset
uspto-grants-2014_11
Patent number
US08877779B2

Reaction notes

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