4-Methoxybenzylamine → HCID 69181089, compound

HRID 1034963Notes

Reaction equation

HRID 1034963 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[CH:11]([C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17])=O.C([BH3-])#N.[Na+]>CO>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:8][CH2:11][C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16]([O:18][CH3:19])=[O:17])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 754524-MethoxybenzylamineHCID 639145Methyl 3-formylbenzoateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 69181089HCID 69181089, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-methoxybenzylamine (5.6 g, 41.2 mmol) in methanol (100 mL) was added methyl 3-formylbenzoate (5.2 g, 31.7 mmol) at ambient temperature. The solution was stirred for 30 minutes and sodium cyanoborohydride (3.0 g) was added. The mixture was stirred at ambient temperature overnight and concentrated to about 20 mL. Water (100 mL) was added and the mixture acidified with 2N hydrochloric acid to a pH of 3. The mixture was partitioned between ethyl acetate and brine and the organic phase separated and concentrated. The residue was purified by flash chromatography on silica gel using 10% methanol in ethyl acetate to give 6.0 g (67%) of the title compound. MS (DCI): m/z 286 (M+H)+.

Workup

  1. stirringThe mixture was stirred at ambient temperature overnight
  2. concentrationconcentrated to about 20 mL
  3. additionWater (100 mL) was added
  4. customThe mixture was partitioned between ethyl acetate and brine
  5. customthe organic phase separated
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel using 10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-9a97b83c4aed4c5396ec2229f10ec8c4
Source dataset
uspto-grants-2013_10
Patent number
US08546368B2

Reaction notes

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