5-Fluorotryptamine → HCID 21071632, compound

HRID 1666867Notes

Reaction equation

HRID 1666867 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=O)[CH2:2][CH3:3].[F:13][C:14]1[CH:25]=[C:24]2[C:17]([NH:18][CH:19]=[C:20]2[CH2:21][CH2:22][NH2:23])=[CH:16][CH:15]=1.[BH4-].[Na+]>CO.COCCOCCOC>[F:13][C:14]1[CH:25]=[C:24]2[C:17](=[CH:16][CH:15]=1)[NH:18][CH:19]=[C:20]2[CH2:21][CH2:22][NH:23][CH2:8][C:7]1[CH:10]=[CH:11][CH:12]=[C:5]([O:4][CH2:1][CH2:2][CH3:3])[CH:6]=1

Participants

6

Reactant 3

HCID 1646825-FluorotryptamineHCID 27604693-PropoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 21071632HCID 21071632, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8150DiglymeSolvent

Procedure

Combine 3-propoxybenzaldehyde (29.6 mg; 0.18 mmol) and 5-fluorotryptamine (14.2 mg; 0.080 mmol) in methanol (2 mL). Add a solution of sodium borohydride in diglyme (1 ml of a 0.5 M solution; 0.50 mmol) and agitate. After 63 h at room temperature concentrate in a stream of nitrogen. Dissolve the residue in methanol and add to a 1 gm SCX column previously rinsed pith 5% acetic acid in methanol. Elute the product from the SCX column with 1 M ammonia in methanol to give the title compound: MS (ES+): m/e (M+1); HPLC (10-90% water/acetonitrile over 10 min, Tr=4.08 min.

Workup

  1. concentrationAfter 63 h at room temperature concentrate in a stream of nitrogen
  2. dissolutionDissolve the residue in methanol
  3. additionadd to a 1 gm SCX column previously rinsed pith 5% acetic acid in methanol
  4. washElute the product from the SCX column with 1 M ammonia in methanol

Sources & evidence

ORD record
ord-4ac209819fff4db49710abe465da9b90
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

Loading…