Phenethylamine → HCID 59730238, compound

HRID 131017Notes

Reaction equation

HRID 131017 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]=O)=[CH:14][CH:13]=2)=[N:7][CH:6]=1)[CH3:2].COC(OC)OC.[CH2:28]([NH2:36])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[BH4-].[Na+]>CO>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][NH:36][CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:14][CH:13]=2)=[N:7][CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 9005Trimethyl orthoformateHCID 4311764Sodium borohydrideHCID 59730157HCID 59730157, compound

Product 1

HCID 59730238HCID 59730238, compoundYield 110.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 6-(4-Formyl-phenoxy)-nicotinic acid ethyl ester (0.62 g, 2.29 mmol), MeOH (12 mL), Trimethylorthoformate (8 mL), and Phenethylamine (0.26 mL, 2.06 mmol). After the reaction stirs at room temperature under a Nitrogen atmosphere for 3.5 hours, add NaBH4 (251.0 mg, 2.75 mmol). After the reaction stirs at room temperature for 12 hours, concentrate under reduced pressure and add the mixture to a 5 g SCX column. Wash the column with MeOH and elute with 1N NH3 MeOH to afford 854.0 mg (99% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 2.8 (2H, t), 2.8-3.0 (4H, m), 3.8 (2H, s), 3.9 (3H, s), 6.9 (1H, d), 7.1-7.4 (9H, m), 8.3 (1H, d), 8.8 (1H, s); MS m/z 377 (M+1).

Workup

  1. waitAfter the reaction stirs at room temperature for 12 hours
  2. concentrationconcentrate under reduced pressure
  3. additionadd the mixture to a 5 g SCX column
  4. washWash the column with MeOH
  5. washelute with 1N NH3 MeOH

Sources & evidence

ORD record
ord-d4bca42d8daa41878692bcbe62b75ab9
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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