Pentane → HCID 18671683, compound

HRID 1057640Notes

Reaction equation

HRID 1057640 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH2:7][C:6](=[O:15])[C:5]2=1.CCCCC.[H-].[Na+].[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1>CN(C=O)C>[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][N:11]2[C:10]3[CH2:9][CH2:8][CH2:7][C:6](=[O:15])[C:5]=3[C:4]3[C:12]2=[CH:13][CH:14]=[C:2]([CH3:1])[CH:3]=3)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 8003PentaneHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 3357026-Methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one

Product 1

HCID 18671683HCID 18671683, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

6-Methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one (0.5457 g, 0.027 mol) is added to a slurry of pentane-washed NaH (0.1369 g, 0.0034 mol) in DMF (3 mL) and after stirring for 20 min, p-fluorobenzyl bromide (0.42 mL, 0.0034 mol) is added, followed by additional DMF (2 mL). After the slurry had stirred for 2.5 h, it is partitioned between water and ethyl acetate. The combined organic layers are washed with water, dried over sodium sulfate and concentrated to dryness. The resulting solids are chromatographed on silica gel (200 mL) using dichloromethane (100%) to give 0.6929 g (82%) of the title compound. An aliquot is recrystallized from ethyl acetate/heptane; mp 209.5-210° C.; MS (ESI+) for C20H18FNO m/z 308.2 (M+H)+; IR (drift) 2939, 1629, 1510, 1467, 1449, 1413, 1362, 1225, 1219, 1190, 1158, 1107, 1094, 832, 797 cm−1; 1H NMR (CDCl3) δ2.23, 2.47, 2.59, 2.85, 5.27, 6.99, 7.05, 7.12, 8.11. Anal. Calcd for C20H18FNO: C, 78.15; H, 5.90; N, 4.56. Found: C, 77.64; H, 5.87; N, 4.44.

Workup

  1. stirringAfter the slurry had stirred for 2.5 h
  2. customit is partitioned between water and ethyl acetate
  3. washThe combined organic layers are washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe resulting solids are chromatographed on silica gel (200 mL)

Sources & evidence

ORD record
ord-167383d4e04a46e7929c905ec6b12ced
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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