3-Bromo-4,5-dimethoxybenzaldehyde → HCID 24955180, compound

HRID 1801613Notes

Reaction equation

HRID 1801613 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[CH:5]=O.[C:14]1([C@H:20]([NH2:22])[CH3:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[BH3-]C#N.[Na+]>CO>[CH3:11][O:10][C:9]1[CH:8]=[CH:7][C:4]([C:2]2[CH:3]=[C:4]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=2[O:10][CH3:11])[CH2:5][NH:22][C@@H:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:21])=[CH:3][CH:2]=1.[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[CH2:5][NH:22][C@@H:20]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:21]

Participants

6

Reactant 3

HCID 813793-Bromo-4,5-dimethoxybenzaldehydeHCID 6431891-Phenethylamine, (+)-HCID 5003444Sodium cyanoborohydride

Product 2

HCID 24955180HCID 24955180, compoundHCID 40761829HCID 40761829, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-bromo-4,5-dimethoxybenzaldehyde 111 (5.0 g, 0.020 mol, Aldrich), (R)-1-phenylethanamine (2.6 mL, 0.020 mol, Aldrich) and ACQH (5.0 mL) in 70 mL of MeOH was stirred at room temp. for 2 hours. The solution was then cooled to 0° C. and NaBH3CN solid was added in portions. The reaction solution was then warmed up to room temp and continued to stir overnight. The mixture was concentrated in vacuo and re-dissolved in 150 mL of EtOAc. The organic solution was washed with 50 mL of saturated. NaHCO3 followed by 50 mL of brine, dried over Na2SO4 and concentrated in vacuo. The residue was passed through a short silica gel pad (eluted with 50% EtOAc/hex). The eluant was concentrated in vacuo to give a light yellow oil, which solidified upon standing to give desired product (R)—N-(3-bromo-4,5-dimethoxybenzyl)-1-phenylethanamine 112 as white waxy solid (5.1 g, 73%). MS (ESI, pos. ion) m/z: 350.2 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 7.4-7.5 (m, 5H); 6.9 (s, 1H); 7.0 (s, 1H), 3.9 (s, 3H); 3.8 (s, 3H); 3.7-3.9 (m, 3H); 1.7 (d, J=7.0 Hz, 3H).

Workup

  1. temperatureThe reaction solution was then warmed up to room temp
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutionre-dissolved in 150 mL of EtOAc
  4. washThe organic solution was washed with 50 mL of saturated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. washThe residue was passed through a short silica gel pad (eluted with 50% EtOAc/hex)
  8. concentrationThe eluant was concentrated in vacuo
  9. customto give a light yellow oil, which

Sources & evidence

ORD record
ord-0de07148d348420f9f72c70d1c509eea
Source dataset
uspto-grants-2013_01
Patent number
US08349831B2

Reaction notes

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