Tryptamine → 1-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

HRID 454955Notes

Reaction equation

HRID 454955 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:20][CH2:21][NH2:22])=[CH:12]1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]2[C:12]3[NH:11][C:19]4[C:14]([C:13]=3[CH2:20][CH2:21][NH:22]2)=[CH:15][CH:16]=[CH:17][CH:18]=4)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1150TryptamineHCID 6422Trifluoroacetic acidHCID 312444-Methoxybenzaldehyde

Product 1

HCID 1989161-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0.5 M solution of 4-methoxybenzaldehyde in dichloromethane (800 μl) was added a 0.25 M solution of 2-(1H-indol-3-yl)ethanamine in dichloromethane (800 μl) followed by trifluoracetic acid (20 μl). The mixture was sealed and shaken at room temperature for 24 hours. The mixture was evaporated to dryness resuspended in toluene (1 ml) vortexed and re-evaporated to dryness. To the residue was added methanol (1.5 ml) and dichloromethane (1 ml). After vortexing the solution was filtered through a pre-washed (methanol, 5 ml) SCX cartridge (Bakerbond JT7090-07, aromatic sulfonic acid). 1-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole, was eluted from the cartridge with 0.5 M aqueous ammonia in methanol (5 ml). Evaporation to dryness gave 1-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole that was used directly for the next step.

Workup

  1. customThe mixture was sealed
  2. customThe mixture was evaporated to dryness
  3. customre-evaporated to dryness
  4. additionTo the residue was added methanol (1.5 ml) and dichloromethane (1 ml)
  5. filtrationwas filtered through
  6. washa pre-washed (methanol, 5 ml) SCX cartridge (Bakerbond JT7090-07, aromatic sulfonic acid)
  7. wash1-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole, was eluted from the cartridge with 0.5 M aqueous ammonia in methanol (5 ml)
  8. customEvaporation to dryness

Sources & evidence

ORD record
ord-3bae1bbb01aa4cb3a30f761f37a8c17a
Source dataset
uspto-grants-2013_07
Patent number
US08497276B2

Reaction notes

Loading…