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Iminodibenyl → methyl 3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-ylmethyl)benzoate

HRID 249161
Notes
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Reaction equation

HRID 249161 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].Cl[CH2:23][C:24]1[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=1)[C:27]([O:29][CH3:30])=[O:28]>O1CCCC1>[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[N:6]([CH2:23][C:24]3[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=3)[C:27]([O:29][CH3:30])=[O:28])[C:5]=2[CH:4]=[CH:3][CH:2]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10308IminodibenylHCID 3248988Methyl 3-(chloromethyl)benzoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 19024806methyl 3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-ylmethyl)benzoateYield 25.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 10,11-dihydro-5H-dibenz[b,f]azepine (2.44 g) in tetrahydrofuran (25 ml) was added potassium tert-butoxide (2.02 g) at 0° C. The mixture was stirred at 0° C. for 15 minutes, and then a solution of methyl 3-(chloromethyl)benzoate (3.57 g) in tetrahydrofuran (15 ml) was added. The mixture was stirred at 25° C. for 1 hour, and then evaporated. The residue was partitioned between ethyl acetate and 0.1N hydrochloric acid. The organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate (40:1) to give methyl 3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-ylmethyl)benzoate (1.10 g) as an oil.

Workup

  1. stirringThe mixture was stirred at 25° C. for 1 hour
  2. customevaporated
  3. customThe residue was partitioned between ethyl acetate and 0.1N hydrochloric acid
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel eluting with a mixture of hexane and ethyl acetate (40:1)

Sources & evidence

ORD record
ord-5a0392a55da541ecb4f9f07138614fca
Source dataset
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05212320

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes