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

HRID 710234
Notes
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Reaction equation

HRID 710234 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 7243O-PhenylenediamineHCID 656671Sodium PyrosulfiteHCID 87320997Tert-butyl 2-(4-formylphenyl)morpholine-4-carboxylate

Product 1

HCID 131733926tert-Butyl 2-(4-(1H-benzo[d]imidazol-2-yl)phenyl)morpholine-4-carboxylateYield 85.2%

Reagents, catalysts & solvents 1

HCID 31374
Dimethylacetamide
Solvent

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

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes