Acetic Acid → N-Benzyl-3-(5-fluoro-1H-indol-3-yl)-cyclopentylamine

HRID 1724701Notes

Reaction equation

HRID 1724701 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:15][CH2:14][C:13](=O)[CH2:12]1.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>[OH-].[Na+]>[CH2:17]([NH:24][CH:13]1[CH2:14][CH2:15][CH:11]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=3)[NH:7][CH:6]=2)[CH2:12]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 221394665-Fluoro-3-(3-oxycyclopentyl)indole

Product 1

HCID 22149137N-Benzyl-3-(5-fluoro-1H-indol-3-yl)-cyclopentylamineYield 105.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture 3-(5-fluoro-1H-indol-3-yl)-cyclopentanone (1.0 g, 4.61 mmol), benzylamine (0.54 g, 5.05 mmol) and glacial acetic acid (0.7 mL, 1.08 mmol) were stirred at room temperature for 30 min. Sodium triacetoxyborohydride (1.5 g, 7.11 mmole) was added portionwise over a 10 min period. The reaction was stirred at room temperature for 24 hours. The reaction mixture was poured into 1 N aqueous NaOH (80 mL) and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with H2O (100 mL) and brine (100 mL), then were dried over anhydrous sodium sulfate, filtered and concentrated to give 1.5 g of a thick yellow oil. Flash chromatography on silica gel (7% 2 M NH3 in methanol/ethyl acetate) afforded 0.5 g of the cis isomer (first eluting) and 0.5 g of the trans isomer.

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washThe combined organic layers were washed with H2O (100 mL) and brine (100 mL)
  3. dry with materialwere dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-71694ad1375b4e448263a3623cd56ee8
Source dataset
uspto-grants-2009_02
Patent number
US07488751B2

Reaction notes

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