Oxalic Acid → HCID 21071628, compound

HRID 1666905Notes

Reaction equation

HRID 1666905 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 4A (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-9da9f32cea4c4a51839db5d661164b92
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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