Triethylamine → 2-Methyl-4-(2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)benzonitrile

HRID 347651Notes

Reaction equation

HRID 347651 reaction equation
[NH:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:12]([C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][C:15]=1[CH3:23])#[N:13].C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1>[C:12]([C:14]1[CH:22]=[CH:21][C:17]([C:18]([N:1]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:19])=[CH:16][C:15]=1[CH3:23])#[N:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5765032,3,4,5-tetrahydro-1H-1-benzazepineHCID 102410994-Cyano-3-methylbenzoic acid

Product 1

HCID 158960852-Methyl-4-(2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,3,4,5-tetrahydro-1H-1-benzazepine (0.80 g, 5.44 mmol) in dichloromethane (40 ml) were added 4-cyano-3-methylbenzoic acid from example C (0.96 g, 5.95 mmol), triethylamine (0.76 g, 5.44 mmol), 4-(dimethylamino)pyridine (0.66 g, 5.44 mmol) and WSCDI (2.17 g, 10.88 mmol). The mixture was stirred at reflux for 18 h, cooled and evaporated in vacuo. The residue was partitioned between EtOAc and 1M KHSO4. The organic layer was washed with saturated sodium bicarbonate solution and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica (eluant EtOAc:pet. ether 30:70); yield 1.10 g (70%).

Workup

  1. temperatureat reflux for 18 h
  2. temperaturecooled
  3. customevaporated in vacuo
  4. customThe residue was partitioned between EtOAc and 1M KHSO4
  5. washThe organic layer was washed with saturated sodium bicarbonate solution and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica (eluant EtOAc:pet. ether 30:70)

Sources & evidence

ORD record
ord-0325dbc96c4643d1a6491018b463c631
Source dataset
uspto-grants-2007_02
Patent number
US07176195B2

Reaction notes

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