Phenethylamine → HCID 44434950, compound

HRID 130738Notes

Reaction equation

HRID 130738 reaction equation
[CH:1]([C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)=O.[CH2:19]([NH2:27])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[BH4-].[Na+]>CO>[CH2:19]([NH:27][CH2:1][C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 4311764Sodium borohydrideHCID 28825277HCID 28825277, compound

Product 1

HCID 44434950HCID 44434950, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 4-(4-Formyl-phenoxy)-benzamide (from Example 247, step 2)(0.39 g, 1.6 mmol), phenethylamine (0.15 g, 1.2 mmol), 20 mL of methanol and 2 g of 3 {acute over (Å)} molecular sieves, and stir at ambient temperature under nitrogen for 5 h. Add sodium borohydride (0.18 g, 4.8 mmol), and stir at ambient temperature for 18 h at ambient temperature. Filter the reaction mixture through Celite, and adsorb on silica gel. Purify by Biotage Flash 40S, eluting with 95:5:0.5 chloroform/ethanol/ammonium hydroxide to afford 0.27 g (93%) of the title compound: mass spectrum (ion spray): m/z=347.28 (M+1); HPLC retention time: 6.01 min (HPLC method in this experiment and subsequent experiments: 5:95-95:5 ACN/0.1% TFA in water over 10 minutes using a 15 cm Zorbax column, running at 1 mL/minute, ultraviolet detector set at 254 nM).

Workup

  1. filtrationFilter the reaction mixture through Celite
  2. customPurify by Biotage Flash 40S
  3. washeluting with 95:5:0.5 chloroform/ethanol/ammonium hydroxide

Sources & evidence

ORD record
ord-a68d27ba195647ffaa850885359898ec
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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