Oxalic Acid → HCID 21071628, compound

HRID 1371976Notes

Reaction equation

HRID 1371976 reaction equation
[CH2:1]([O:8][C:9]1[CH:20]=[C:19]2[C:12]([NH:13][CH:14]=[C:15]2[CH2:16][CH2:17][NH2:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:21]([C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH:31]=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[BH4-].[Na+].C(O)(=O)C(O)=O>CO.O>[CH2:1]([O:8][C:9]1[CH:20]=[C:19]2[C:12](=[CH:11][CH:10]=1)[NH:13][CH:14]=[C:15]2[CH2:16][CH2:17][NH:18][CH2:31][C:30]1[CH:33]=[CH:34][CH:35]=[C:28]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:29]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 382843-PhenoxybenzaldehydeHCID 895762-[5-(Benzyloxy)-1H-indol-3-yl]ethan-1-amineHCID 4311764Sodium borohydride

Product 1

HCID 21071628HCID 21071628, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 962WaterSolvent

Procedure

Combine 5-benzyloxy tryptamine (1.23 g, 4.6 mmol), 3-phenoxybenzaldehyde (97%, 1.09 g, 5.53 mmol) and molecular sieves 4 A (1.0 g) and stir in methanol (15 mL) for 4 h. Filter the molecular sieves and wash several times with MeOH. To this MeOH solution, add portionwise NaBH4 (174 mg, 4.60 mmol), stir the resulting mixture at room temperature for 1 h. Remove MeOH under vacuum, dilute the residue with CH2CL2/water, extract with CH2Cl2, combine organic layers, dry over Na2SO4 and concentrate the solvent in vacuo. Purification by silica gel chromatography(CH2Cl2/MeOH) to give the free base. Combine the free base with oxalic acid to form the salt: (300 MHz, DMSO-d6) 2.95–3.15 (m, 4H), 3.93 (s, 2H), 4.10 (br, 1H), 5.05 (s, 2H), 6.85–7.46 (m, 18H), 10.67 (br, 1H); ms (ELECTROSPRAY) m/e: 449.2 (M+1).

Workup

  1. filtrationFilter the molecular sieves
  2. washwash several times with MeOH
  3. extractionextract with CH2Cl2
  4. dry with materialdry over Na2SO4
  5. concentrationconcentrate the solvent in vacuo
  6. customPurification by silica gel chromatography(CH2Cl2/MeOH)
  7. customto give the free base
  8. customto form the salt

Sources & evidence

ORD record
ord-3928982b5326467aac7fddc6b69d3982
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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