Water → tert-Butyl 2-(4-(1H-benzo[d]imidazol-2-yl)phenyl)morpholine-4-carboxylate

HRID 710234Notes

Reaction equation

[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)=[CH:5][CH:4]=1)=O.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH2:29].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].O>CC(N(C)C)=O>[NH:22]1[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[N:29]=[C:1]1[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 90 °C

Procedure

tert-Butyl 2-(4-formylphenyl)morpholine-4-carboxylate (300 mg, 1.03 mmol) was dissolved in dimethylacetamide (4.5 ml). 1,2-Diaminobenzene (134 mg, 1.24 mmol) and sodium metabisulfite (294 mg, 1.54 mmol) were added and the reaction mixture was stirred at 90° C. overnight. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over MgSO4 and evaporated. The crude material was purified by flash chromatography (20 g silica gel, 40 to 70% ethyl acetate in heptane) to yield a white solid (333 mg, 85%). MS (ISP): 280.3 (100%, [M-BOC+H]+), 380.2 (20%, [M+H]+).

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over MgSO4
customevaporated
customThe crude material was purified by flash chromatography (20 g silica gel, 40 to 70% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-3f9f9993d34543faab8c9271b21f29fd
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181230B2

Reaction notes

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