Water → HCID 23298448, compound

HRID 2393552Notes

Reaction equation

HRID 2393552 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 (250 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-eed3b0d4d2014489b1c742d74ed0e52b
Source dataset
uspto-grants-1998_09
Patent number
US05807886

Reaction notes

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