Emedastine → 1-ethoxycarbonyl-4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane

HRID 637017

Reaction equation

C[N:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[N:13]([CH2:14][CH2:15][O:16][CH2:17][CH3:18])[C:12]3[CH:19]=[CH:20][CH:21]=[CH:22][C:11]=3[N:10]=2)[CH2:4][CH2:3]1.Cl[C:24]([O:26][CH2:27][CH3:28])=[O:25]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:27]([O:26][C:24]([N:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[N:13]([CH2:14][CH2:15][O:16][CH2:17][CH3:18])[C:12]3[CH:19]=[CH:20][CH:21]=[CH:22][C:11]=3[N:10]=2)[CH2:4][CH2:3]1)=[O:25])[CH3:28]

Participants

Conditions

Temperature: 80 °C

Procedure

Combine 1-methyl-4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane (1.79 g, 5.9 mmol) and ethyl chloroformate (0.75 mL, 7.8 mmol) in toluene (20 mL). Heat to 80° C. After 2 hours, cool the reaction mixture and dilute with ethyl acetate. Extract with a saturated aqueous sodium bicarbonate solution, dry the organic layer over MgSO4, filter, and evaporate in vacuo to give 1-ethoxycarbonyl-4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane: Rf=0.87 (silica gel, dichloromethane/methanol, 90/10).

Workup

temperaturecool the reaction mixture
extractionExtract with a saturated aqueous sodium bicarbonate solution
dry with materialdry the organic layer over MgSO4
filtrationfilter
customevaporate in vacuo

Sources & evidence

ORD record: ord-15801f908389420a9fd553964f908d06
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06194406B1

Linked notes

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