Morpholine → methyl 3-(morpholin-4-ylmethyl)benzoate

HRID 880314Notes

Reaction equation

HRID 880314 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=O.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.[BH3-]C#N.[Na+]>CO>[O:16]1[CH2:17][CH2:18][N:13]([CH2:1][C:3]2[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=2)[C:6]([O:8][CH3:9])=[O:7])[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 639145Methyl 3-formylbenzoateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 437850methyl 3-(morpholin-4-ylmethyl)benzoateYield 90,579.602%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of methyl 3-formylbenzoate (100 mg, 0.61 mmol) in MeOH (5 mL) was added morpholine (100 mg, 1.15 mmol) and the resulting mixture was stirred for 10 min at 20° C. To the mixture was added NaBH3CN (100 mg, 1.59 mmol) and the reaction mixture was stirred for 30 min at 20° C. The solution was concentrated and the residue was purified by prep-TLC to afford the title compound (130 g, Yield 90.9%). 1H NMR (CD3OD, 400 MHz): δ 7.98-8.05 (m, 1H), 7.92 (td, J=1.4, 7.7 Hz, 1H), 7.57-7.62 (m, 1H), 7.37-7.53 (m, 1H), 3.90 (s, 3H), 3.66-3.71 (m, 4H), 3.57 (s, 2H), 2.41-2.49 (m, 4H).

Workup

  1. stirringthe reaction mixture was stirred for 30 min at 20° C
  2. concentrationThe solution was concentrated
  3. customthe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-ef6f69ab332e4d7abb522a5e4185a33b
Source dataset
uspto-grants-2015_03
Patent number
US08993555B2

Reaction notes

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