Isoamylamine → 2-Bromo-4-((isopentylamino)methyl)phenol

HRID 1182052Notes

Reaction equation

HRID 1182052 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=O.[CH3:11][CH:12]([CH3:16])[CH2:13][CH2:14][NH2:15].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][NH:15][CH2:14][CH2:13][CH:12]([CH3:16])[CH3:11])[CH:7]=[CH:8][C:9]=1[OH:10]

Participants

5

Reactant 3

HCID 7894IsoamylamineHCID 763083-Bromo-4-hydroxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 589380042-Bromo-4-((isopentylamino)methyl)phenolYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Combine 3-Bromo-4-hydroxy-benzaldehyde (1.5 g, 7.5 mmol) with 3-methylbutylamine (867 μL, 7.5 mmol), MeOH (25 mL) and molecular sieves 3A (5.8 g) and stir at room temperature overnight. Add NaBH4 (1.4 g, 37.3 mmol) and stir at room temperature for 2 hours. Filtrate over celite with MeOH and eliminate the solvent. Purify by SCX ion-exchange chromatography to afford the title compound (1.5 g, 75%). 1H-NMR (CD3OD, 300 MHz): 7.52 (d, 1H, J=2.0 Hz), 7.17 (dd, 1H, J=2.0 and 8.5 Hz), 6.87 (d, 1H, J=8.5 Hz), 3.80 (s, 2H), 2.79-2.74 (m, 2H), 1.76-1.63 (m, 1H), 1.54 (q, 2H, J=6.8 Hz), 0.99 (d, 6H, J=6.56 Hz). 13C-NMR (CD3OD, 300 MHz): 158.6, 134.9, 130.7, 128.6, 118.8, 112.7, 53.3, 47.9, 38.6, 27.8, 23.3.

Workup

  1. customPurify by SCX ion-exchange chromatography

Sources & evidence

ORD record
ord-2b5bfd974d79454992ee8e699bfd331b
Source dataset
uspto-grants-2007_10
Patent number
US07288543B2

Reaction notes

Loading…