4-Methylmorpholine → N-benzyl-N-phenyl-2-benzyloxy-5-formylbenzamide

HRID 1583032Notes

Reaction equation

HRID 1583032 reaction equation
[C:1]1([NH:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:15]([O:22][C:23]1[CH:31]=[CH:30][C:29]([CH:32]=[O:33])=[CH:28][C:24]=1[C:25](O)=[O:26])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.ON1C2N=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[CH2:8]([N:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:25](=[O:26])[C:24]1[CH:28]=[C:29]([CH:32]=[O:33])[CH:30]=[CH:31][C:23]=1[O:22][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 66028BenzylanilineHCID 181649HOAtHCID 9698702-(Benzyloxy)-5-formylbenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 22716810N-benzyl-N-phenyl-2-benzyloxy-5-formylbenzamideYield 37%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

N-Phenylbenzylamine (0.72 g, 3.9 mmol, 2 eq) was added to a solution of 2-benzyloxy-5-formylbenzoic acid (500 mg, 1.95 mmol, 1 eq), 1-hydroxy-7-azabenzotriazole (530 mg, 3.9 mmol, 2 eq), and N-methylmorpholine (0.58 mL, 5.3 mmol, 2.73 eq) in N,N-dimethylformamide (10 mL). To this was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (750 mg, 13.9 mmol, 2 eq) and the stirred reaction mixture was heated overnight at 50° C. The reaction mixture was diluted with ethyl acetate (20 mL) and washed sequentially with 10% HCl (3×20 mL), brine (20 mL), saturated aqueous sodium bicarbonate (2×20 mL) and brine (20 mL). The organic solution was dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica with petroleum ether:ethyl acetate (3:1) as eluent, to give the product as a white powder (300 mg, 37%). RF (petroleum ether:ethyl acetate 1:1) 0.55. 1H NMR (CDCl3) δ9.78 (s, 1H, O═C—H), 5.08 (s, 2H, OCH2Ph), 5.02 (s, 2H, NCH2Ph).

Workup

  1. customthe stirred reaction mixture
  2. washwashed sequentially with 10% HCl (3×20 mL), brine (20 mL), saturated aqueous sodium bicarbonate (2×20 mL) and brine (20 mL)
  3. dry with materialThe organic solution was dried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica with petroleum ether:ethyl acetate (3:1) as eluent

Sources & evidence

ORD record
ord-0da3775490bc48c3a85351c3482992f0
Source dataset
uspto-grants-2004_05
Patent number
US06740670B2

Reaction notes

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