Triethylamine → [3-(7-Methoxy-indol-1-yl)-3-pyridin-3-yl-propyl]-methyl-amine

HRID 250211Notes

Reaction equation

HRID 250211 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[N:10]([CH:12]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[CH2:13][CH2:14]O)[CH:9]=[CH:8]2.[CH2:22]([N:24](CC)CC)C.CS(Cl)(=O)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[N:10]([CH:12]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[CH2:13][CH2:14][NH:24][CH3:22])[CH:9]=[CH:8]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 580884743-(7-Methoxy-indol-1-yl)-3-pyridin-3-yl-propan-1-ol

Product 1

HCID 58088483[3-(7-Methoxy-indol-1-yl)-3-pyridin-3-yl-propyl]-methyl-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(7-methoxy-indol-1-yl)-3-pyridin-3-yl-propan-1-ol in dichloromethane (10 ml) was added triethylamine (0.086 g) followed by methanesulfonyl chloride (0.071 g) dropwise at 0° C. The mixture was stirred for 30 minutes at the same temperature and then the reaction was quenched by partitioning between water and dichloromethane. The organic layer was washed with bicarbonate solution, dried and evaporated to dryness. The crude product was taken up in an ethanolic solution of methyl amine (33%, 4 ml), stirred for 30 minutes at room temperature and then at 100° C. in a microwave reactor. After cooling, the solvents were removed, the crude product was partitioned between dichloromethane and bicarbonate solution, and the organic layer separated. The resulting residue was purified by chromatography on silica gel eluting with mixtures of dichloromethane, methanol and ammonium hydroxide to give 0.088 g of [3-(7-methoxy-indol-1-yl)-3-pyridin-3-yl-propyl]-methyl-amine.

Workup

  1. customthe reaction was quenched
  2. customby partitioning between water and dichloromethane
  3. washThe organic layer was washed with bicarbonate solution
  4. customdried
  5. customevaporated to dryness
  6. stirringstirred for 30 minutes at room temperature
  7. customat 100° C.
  8. temperatureAfter cooling
  9. customthe solvents were removed
  10. customthe crude product was partitioned between dichloromethane and bicarbonate solution
  11. customthe organic layer separated
  12. customThe resulting residue was purified by chromatography on silica gel eluting with mixtures of dichloromethane, methanol and ammonium hydroxide

Sources & evidence

ORD record
ord-7a6845032e65428f9ed5b15e685c2b36
Source dataset
uspto-grants-2011_01
Patent number
US07863305B2

Reaction notes

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