Dibenzylamine → HCID 3133123, compound

HRID 2268135Notes

Reaction equation

HRID 2268135 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH:11]2[O:13][CH2:12]2)=[CH:5][CH:4]=1.[CH2:14]([NH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[CH2:22]([N:21]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:12][CH:11]([OH:13])[CH2:10][O:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 7656DibenzylamineHCID 166462,3-Epoxypropyl 4'-methoxyphenyl ether

Product 1

HCID 3133123HCID 3133123, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of glycidyl 4-methoxyphenyl ether (1.10 g, 6.10 mmol), dibenzylamine (1.25 g, 6.33 mmol), and anhydrous ethyl alcohol (20 mL) was heated at 80° C. for 2 days. The solvent was evaporated under reduced pressure to give the title compound as a clear oil (2.36 g, 100%). 1H NMR (CDCl3) δ7.35-7.30 (m, 7 H), 7.28-7.25 (m, 3 H), 6.82-6.76 (m, 4 H), 4.10-4.07 (m 1 H), 3.83-3.81 (m, 3 H), 3.78-3.76 (m, 1 H), 3.76 (s, 3 H), 3.53 (d, 2 H, J=13.4 Hz), 2.66 (d, 2 H, J=6.5 Hz). Mass spectrum (LCMS, ESI) calcd. for C24H27NO3: 378 (M+H). Found: 378.

Workup

  1. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b5ff2555f2fc4fbb9d184cd477fa5171
Source dataset
uspto-grants-2001_12
Patent number
US06326492B1

Reaction notes

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