4-Hydroxybenzaldehyde → HCID 3142011, compound

HRID 1611556Notes

Reaction equation

HRID 1611556 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[OH:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:18]1([C:17]2[CH:20]=[CH:21][C:14]([OH:13])=[CH:15][CH:16]=2)[C:5]2[NH:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4]=2[CH2:3][CH2:2][NH:1]1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 1150TryptamineHCID 6422Trifluoroacetic acid

Product 1

HCID 3142011HCID 3142011, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tryptamine (5.0 g, 31.2 mmole) in dry CH2Cl2 (100 mL) at RT was added 4-hydroxybenzaldehyde (3.81 g, 31.2 mmole) followed by dropwise addition of trifluoroacetic acid (7.11 g, 62.4 mmole). After 12 hr, the reaction solution was washed with 10% aqueous NaHCO3 (100 mL), H2O (100 mL) and brine. The organic solution was dried over Na2SO4 and concentrated under reduced pressure to give a yellow oil. The yellow residue was washed with hexanes and dried under high vacuum to afford the title compound (7.74 g, 94%) as a light yellow solid: MS (ES) m/e 265 (M+H)+.

Workup

  1. washthe reaction solution was washed with 10% aqueous NaHCO3 (100 mL), H2O (100 mL) and brine
  2. dry with materialThe organic solution was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customto give a yellow oil
  5. washThe yellow residue was washed with hexanes
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-78cffadbd2594949a08532eaf4c003bf
Source dataset
uspto-grants-2006_01
Patent number
US06987115B2

Reaction notes

Loading…