Acetic Acid → 5-Nitro-2-(phenylmethyl)aminoindane

HRID 2393542Notes

Reaction equation

HRID 2393542 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C:8](=O)[CH2:7]2)([O-:3])=[O:2].[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([NH:21][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:7]2)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 15020665-Nitro-2-indanoneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 232110515-Nitro-2-(phenylmethyl)aminoindane

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5-Nitro-2-indanone (1.48 g, 8.36 mmol), benzylamine (4.40 ml, 41.8 mmol), acetic acid (15.0 ml), 4 Å molecular sieves (20 ml), THF (15 ml), and MeOH (15 ml) were introduced into a flask and cooled to 0° C. Sodium cyanoborohydride (1.05 g, 16.7 mmol) was then added portionwise over a 5-minute period. The mixture was stirred for 14 hr, filtered through celite, and concentrated to a syrup. The mixture was made basic with 2N NaOH and extracted with ether (3×50 ml). The combined extracts were washed with water, dried over magnesium sulfate, filtered, concentrated and chromatographed over silica gel (3% methanol/methylene chloride) to yield 5-nitro-2-(phenylmethyl)aminoindane: (1.18 g, 53%); M.S. (M+H)+ =269.

Workup

  1. filtrationfiltered through celite
  2. concentrationconcentrated to a syrup
  3. extractionextracted with ether (3×50 ml)
  4. washThe combined extracts were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed over silica gel (3% methanol/methylene chloride)

Sources & evidence

ORD record
ord-0c4600a2a1ae4760be8a0674f5d384e7
Source dataset
uspto-grants-1998_09
Patent number
US05807886

Reaction notes

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