Triethylamine → HCID 21083245, compound

HRID 347633Notes

Reaction equation

HRID 347633 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][CH:15]=1)#[N:13].C(N(CC)CC)C>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][CH:15]=1)#[N:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 120874-Cyanobenzoic acidHCID 5765032,3,4,5-tetrahydro-1H-1-benzazepine

Product 1

HCID 21083245HCID 21083245, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of 2,3,4,5-tetrahydro-1H-1-benzazepine (1.05 g, 7.14 mmol) in dichloromethans (40 ml) were added 4-cyanobenzoic acid (1.26 g, 8.57 mmol), triethylamine (1.00 g, 7.14 mmol), 4-(dimethylamino)pyridine (0.87 g, 7.14 mmol) and WSCDI (2.86 g, 14.28 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 to give a white solid; yield 1.50 g (76%).

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. customto give a white solid

Sources & evidence

ORD record
ord-299cf132274b4f57a0d398e708e6d702
Source dataset
uspto-grants-2007_02
Patent number
US07176195B2

Reaction notes

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