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

HRID 558944Notes

Reaction equation

HRID 558944 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>[CH3:23][C:15]1[CH:16]=[C:17]([C:18]([N:1]2[CH2:2][CH2:3][CH2:4][CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]2=3)=[O:19])[CH:21]=[CH:22][C:14]=1[C:12]#[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, 5.4 mmol) in dichloromethane (40 ml) were added 4-cyano-3-methylbenzoic acid from Example C (0.96 g, 6.0 mmol), triethylamine (0.75 ml, 5.4 mmol), 4-dimethylaminopyridine (0.66 g, 5.4 mmol) and WSCDI (2.2 g, 11 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 1.1 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-74b60dece3d94a6ba8cacdf7bee67249
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

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