Diisopropylamine → 2-[(Dimethylamino)methyl]-3,4-dihydro-4-methylcyclopent[b]indol-1(2H)-one

HRID 2165115Notes

Reaction equation

HRID 2165115 reaction equation
C([Li])CCC.[CH:6]([NH:9][CH:10](C)C)(C)C.[CH3:13][N:14]1[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:16]2[C:23](=[O:26])[CH2:24][CH2:25][C:15]1=2.[I-].[CH3:28]C=[N+]=CC>C1COCC1>[CH3:6][N:9]([CH2:10][CH:24]1[CH2:25][C:15]2[N:14]([CH3:13])[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:16]=2[C:23]1=[O:26])[CH3:28]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 118162844-methyl-2,3-dihydrocyclopenta[b]indol-1(4H)-oneHCID 21892197N,N-dimethylmethyleneammoniumiodideHCID 178418339Butyllithium

Product 1

HCID 230437832-[(Dimethylamino)methyl]-3,4-dihydro-4-methylcyclopent[b]indol-1(2H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Butyllithium (1.6M in hexane; 3.4 ml) was added dropwise, under nitrogen, at 0° to a stirred solution of diisopropylamine (0.76 ml) in THF (15 ml) and the resulting solution was stirred at 0° for 10 min. before cooling to -78°. A solution of 4-methyl-3,4-dihydrocyclopent[b]indol-1(2H)-one (1 g) in THF (120 ml) was added dropwise at -78° to -70° and the resulting solution was stirred at ca. -78° for 10 min. before N,N-dimethylmethyleneammonium iodide (ca. 1 g) was added. The resulting mixture was allowed to warm to room temperature over 1.5 h and was then partitioned between 2N sodium carbonate (100 ml) and ethyl acetate (2×100 ml). The combined, dried organic extracts were evaporated in vacuo to give an oil which was purified by FCC eluting with System A (100:8:1) to give the title compound (0.14 g) as an oil, t.l.c. (System A 100:8:1) Rf 0.2.

Workup

  1. temperaturebefore cooling to -78°
  2. additionwas added
  3. customwas then partitioned between 2N sodium carbonate (100 ml) and ethyl acetate (2×100 ml)
  4. customdried organic extracts were evaporated in vacuo
  5. customto give an oil which
  6. customwas purified by FCC
  7. washeluting with System A (100:8:1)

Sources & evidence

ORD record
ord-8cc8e3fded5f461fb55c4f7a438d21e6
Source dataset
uspto-grants-1990_07
Patent number
US04939144

Reaction notes

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