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Triethylamine → (E)-3-[4-(2,3,4,5-Tetrahydro-benzo[b]azepine-1-carbonyl)-phenyl]-acrylic Acid Methyl Ester

HRID 220889
Notes
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Reaction equation

HRID 220889 reaction equation
[CH3:1][O:2][C:3](/[CH:5]=[CH:6]/[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1)=[O:4].[NH:16]1[CH2:22][CH2:21][CH2:20][CH2:19][C:18]2[CH:23]=[CH:24][CH:25]=[CH:26][C:17]1=2.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[CH3:1][O:2][C:3](=[O:4])/[CH:5]=[CH:6]/[C:7]1[CH:8]=[CH:9][C:10]([C:11]([N:16]2[CH2:22][CH2:21][CH2:20][CH2:19][C:18]3[CH:23]=[CH:24][CH:25]=[CH:26][C:17]2=3)=[O:13])=[CH:14][CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5765032,3,4,5-tetrahydro-1H-1-benzazepineHCID 106083304-((1E)-3-methoxy-3-oxoprop-1-en-1-yl)benzoic acid

Product 1

HCID 57555201(E)-3-[4-(2,3,4,5-Tetrahydro-benzo[b]azepine-1-carbonyl)-phenyl]-acrylic Acid Methyl EsterYield 48%

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent

Procedure

WSCD (1.17 g, 6.16 mmol) was added to a solution of 4-((E)-2-methoxycarbonyl-vinyl)-benzoic acid from Example E65.1 (740 mg, 3.59 mmol), 2,3,4,5-tetrahydro-1H-benzo[b]azepine (445 mg, 3.02 mmol) and DMAP (370 mg, 3.02 mmol) in dichloromethane (40 ml) and triethylamine (0.7 ml, 5.02 mmol). The mixture was heated at reflux for 42 h then solvents were concentrated in vacuo. The residue was dissolved in EtOAc, washed with 1M KHSO4 then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 30% EtOAc:70% pet. ether) to yield the title compound (484 mg, 48%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 42 h
  3. concentrationsolvents were concentrated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with 1M KHSO4
  6. dry with materialbrine, dried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel (eluant; 30% EtOAc:70% pet. ether)

Sources & evidence

ORD record
ord-008e0e4bc9b541838f2fecdfa52d7a8d
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08202858B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes