Triethylamine → 5H,6H,7H,8H,9H-pyrido[2,3-d]azepine

HRID 571633Notes

Reaction equation

HRID 571633 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][NH:9][CH2:8][CH2:7][C:6]=2[N:12]=1.C(N(CC)CC)C.[H][H]>[Pd].CO>[N:12]1[C:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 249592722-Chloro-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepineHCID 178418361HCID 178418361, compound

Product 1

HCID 231227435H,6H,7H,8H,9H-pyrido[2,3-d]azepine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under a hydrogen atmosphere 0.125 g (0.49 mmol) 2-chloro-6,7,8,9-tetrahydro-5H-pyri do[2,3-d]azepine, 30 mg palladium on charcoal (10%) and 0.28 mL triethylamine in 4 mL methanol were hydrogenated at RT under 50 psi hydrogen pressure for 6 h. The catalyst was removed and the filtrate was concentrated to dryness. The residue was used without further purification. Yield: 72 mg (99% of theory). ESI-MS: m/z=149 (M+H)+; Rt(HPLC): 0.52 min (Method J).

Workup

  1. customThe catalyst was removed
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe residue was used without further purification

Sources & evidence

ORD record
ord-21bd40b2986b4bd0809451c3c52e86d6
Source dataset
uspto-grants-2015_05
Patent number
US09029360B2

Reaction notes

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