Water → HCID 23298448, compound

HRID 1953545Notes

Reaction equation

HRID 1953545 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH:11]2[NH2:14])=[CH:7][CH:6]=1)([O-:4])=[O:3].C(N(CC)CC)C.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O>CN(C=O)C>[ClH:1].[N+:2]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH:11]2[NH:14][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:7][CH:6]=1)([O-:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 8471TriethylamineHCID 232984006-Nitro-2,3-dihydro-1H-inden-1-amine--hydrogen chloride (1/1)

Product 1

HCID 23298448HCID 23298448, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 6-nitro-1-aminoindane hydrochloride (1.90 g, 8.85 mmol) in DMF (30 ml) was added triethylamine (2.50 ml, 18.06 mmol) followed by benzyl bromide (1.07 ml, 9.03 mmol). The mixture was warmed to room temperature, stirred for 3 hr, dumped into water (100 ml), and extracted with ethyl acetate (3×70 ml). The combined extracts were washed with water, dried over magnesium sulfate, filtered through a small plug of silica gel and reduced to a syrup. The titled compound was isolated as the hydrochloride salt: (1.34 g, 50%); m.p. 234-235° C.

Workup

  1. extractionextracted with ethyl acetate (3×70 ml)
  2. washThe combined extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered through a small plug of silica gel

Sources & evidence

ORD record
ord-a03bdd153d364011a71eadda57534a2f
Source dataset
uspto-grants-2000_09
Patent number
US06117898

Reaction notes

Loading…