Benzylamine → HCID 739191, compound

HRID 1944235Notes

Reaction equation

HRID 1944235 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][C:12]=1[O:19][CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[CH2:1]([NH:8][CH2:15][C:14]1[CH:17]=[CH:18][C:11]([O:10][CH3:9])=[C:12]([O:19][CH3:20])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 8419VeratraldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 739191HCID 739191, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of benzylamine (3.94 mL, 36 mmol) and 4,3-dimethoxybenzaldehyde (5.0 g, 30 mmol) in chloroform (120 mL), was added sodium triacetoxyborohydride (9.53 g, 45 mmol). The mixture was stirred at rt for 18 hrs prior to addition of saturated NaHCO3. The organic phase was separated and the aqueous phase extracted with chloroform. The combined extracts were washed with brine, dried over MgSO4 and evaporated to afford the crude product. Purification by flash column chromatography afforded the title compound as a pale yellow oil (5.47 g, 71%). 1H NMR (270 MHz, CDCl3) δ 3.74 (2H, s), 3.80 (2H, s), 3.86 (3H, s), 3.88 (3H, s), 6.80-6.89 (3H, m), 7.22-7.34 (5H, m); HRMS (ESI+) calcd. for C16H20NO2 (M++H) 258.1489, found 258.1478; LC/MS (ES+) tr=0.79 min, m/z 258.2 (M++H).

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous phase extracted with chloroform
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customto afford the crude product
  7. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-93171533fd1d461baaa631f6eb71d02a
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

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