1H-Indole, 3-(2-aminoethyl)-5-phenoxy- → HCID 21071537, compound

HRID 1666835Notes

Reaction equation

HRID 1666835 reaction equation
[O:1]([C:8]1[CH:19]=[C:18]2[C:11]([NH:12][CH:13]=[C:14]2[CH2:15][CH2:16][NH2:17])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:20]([C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH:30]=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[BH4-].[Na+]>CO.ClCCl.O>[O:1]([C:8]1[CH:19]=[C:18]2[C:11](=[CH:10][CH:9]=1)[NH:12][CH:13]=[C:14]2[CH2:15][CH2:16][NH:17][CH2:30][C:29]1[CH:32]=[CH:33][CH:34]=[C:27]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:28]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 357801H-Indole, 3-(2-aminoethyl)-5-phenoxy-HCID 382843-PhenoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 21071537HCID 21071537, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21908982Water methylene chlorideSolvent

Procedure

Combine 5-phenoxytryptamine (0.400 g, 1.59 mmol), 3-phenoxybenzaldehyde (0.377 g, 1.90 mmol) and molecular sieves 4 Å (0.40 g) in methanol (15 mL) and stir for 4 h. Filter and wash the molecular sieves several times with MeOH. Add NaBH4 (61.5 mg, 1.59 mmol) in portions to the filtrate and stir at room temperature for 1 h. Remove the MeOH under vacuum to give a residue, dilute the residue with dichloromethane/water, separate the layers, extract the aqueous layer with dichloromethane, combine the organic layers, and dry over Na2SO4. Concentrate in vacuo and chromatograph on silica gel eluting with dichloromethane/MeOH the title compound. Form the oxalate salt of the title compound: m.p. 196-198° C.; 1H NMR (300 MHz, DMSO-d6) 2.95-3.15 (m, 4H), 4.15 (s, 2H), 6.85-7.46 (m, 18H), 11.06 (br, 1H); MS (ELECTROSPRAY) m/e: 435.3 (M+1); HRMS (ES+) calcd for C29H27N2O2 (M+H) 435.2084 found 435.2073.

Workup

  1. filtrationFilter
  2. washwash the molecular sieves several times with MeOH
  3. customRemove the MeOH under vacuum
  4. customto give a residue
  5. customseparate the layers
  6. extractionextract the aqueous layer with dichloromethane
  7. dry with materialdry over Na2SO4
  8. concentrationConcentrate in vacuo and chromatograph on silica gel eluting with dichloromethane/MeOH the title compound

Sources & evidence

ORD record
ord-0fc5572eeeb5447c829a3a204f0ccf26
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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