Sodium Iodide → HCID 22859588, compound

HRID 975138Notes

Reaction equation

HRID 975138 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C@H:12]1[CH2:16][CH2:15][CH2:14][NH:13]1.[CH:17]1([CH2:20]Br)[CH2:19][CH2:18]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>COCCOC>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[CH2:20][CH:17]1[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 81503BromomethylcyclopropaneHCID 228595901H-Indole, 5-bromo-3-(2-pyrrolidinylmethyl)-, (R)-

Product 1

HCID 22859588HCID 22859588, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred mixture of 5-bromo-3-(2(R)-pyrrolidinylmethyl)-1H-indole (Preparation 2; 1.84 g, 6.3 mmol), cyclopropylmethyl bromide (0.67 ml, 6.9 mmol), anhydrous sodium carbonate (0.73 g, 6.9 mmol), sodium iodide (1.0 g, 6.7 mmol) and 1,2-dimethoxyethane (10 ml), under nitrogen, was heated under reflux for 14 hours, allowed to cool, then partitioned between ethyl acetate and 2M aqueous sodium carbonate solution. The organic phase was separated, washed with 2M aqueous sodium carbonate solution, dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with 0.880 aqueous ammonia:methanol: dichloromethane (0.05:10:90), to provide the required product as a foam (2.09 g). Rf 0.24 (SS 6). [α]D25 +72° (c=0.1, CH3OH). Found: C,61.22; H,6.40; N,8.39. C17H21BrN2 requires C,61.26; H,6.35; N,8.41%.

Workup

  1. temperatureunder nitrogen, was heated
  2. temperatureunder reflux for 14 hours
  3. temperatureto cool
  4. custompartitioned between ethyl acetate and 2M aqueous sodium carbonate solution
  5. customThe organic phase was separated
  6. washwashed with 2M aqueous sodium carbonate solution
  7. dry with materialdried (Na2SO4)
  8. customevaporated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel
  10. washeluting with 0.880 aqueous ammonia:methanol: dichloromethane (0.05:10:90)

Sources & evidence

ORD record
ord-0ec2ca87d71e4dd0ab754d8ff3a8c627
Source dataset
uspto-grants-1997_03
Patent number
US05607960

Reaction notes

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