Benzylamine → N-Benzyl-3-[4-(2,3,4,5-tetrahydro-benzo[b]azepine-1-carbonyl)-phenyl]-propionamide

HRID 220892Notes

Reaction equation

HRID 220892 reaction equation
[N:1]1([C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22](O)=[O:23])=[CH:16][CH:15]=2)=[O:13])[CH2:7][CH2:6][CH2:5][CH2:4][C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.S(Cl)(Cl)=O.[CH2:29]([NH2:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(N(CC)CC)C>ClCCl>[CH2:29]([NH:36][C:22](=[O:23])[CH2:21][CH2:20][C:17]1[CH:16]=[CH:15][C:14]([C:12]([N:1]2[CH2:7][CH2:6][CH2:5][CH2:4][C:11]3[CH:10]=[CH:9][CH:8]=[CH:3][C:2]2=3)=[O:13])=[CH:19][CH:18]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 575553343-[4-(2,3,4,5-Tetrahydro-benzo[b]azepine-1-carbonyl)-phenyl]-propionic Acid

Product 1

HCID 57555288N-Benzyl-3-[4-(2,3,4,5-tetrahydro-benzo[b]azepine-1-carbonyl)-phenyl]-propionamideYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-[4-(2,3,4,5-tetrahydro-benzo[b]azepine-1-carbonyl)-phenyl]-propionic acid from Example E65.4 (57 mg, 0.18 mmol) and thionyl chloride (0.2 ml, 2.74 mmol) in dichloromethane (6 ml) was heated at reflux for 2 h then volatiles were removed in vacuo. The residue was dissolved in dichloromethane (8 ml) then benzylamine (0.022 ml, 0.20 mmol) and triethylamine (0.05 ml, 0.36 mmol) were added. The mixture was stirred for 3 h at room temperature then concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 30% pet. ether:70% EtOAc) to give a white fluffy solid identified as the title compound (36.5 mg, 50%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. customwere removed in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane (8 ml)
  5. concentrationthen concentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel (eluant; 30% pet. ether:70% EtOAc)
  7. customto give a white fluffy solid

Sources & evidence

ORD record
ord-e43d39b8aa4f445f9908714ec0fef785
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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