Diisopropylethylamine → 4-[5-(2-Pyridinyl)thien-2-ylcarbonyl]-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine

HRID 2255993Notes

Reaction equation

HRID 2255993 reaction equation
[S:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:4]=2[CH:3]=[CH:2]1.C(N(CC)C(C)C)(C)C.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[S:30][C:29]([C:31](Cl)=[O:32])=[CH:28][CH:27]=1>ClCCl.O>[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[S:30][C:29]([C:31]([N:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]3[S:1][CH:2]=[CH:3][C:4]2=3)=[O:32])=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27761995-(2-Pyridinyl)-2-thiophenecarbonyl chlorideHCID 118049715,6,7,8-Tetrahydro-4H-thieno[3,2-B]azepine

Product 1

HCID 214671644-[5-(2-Pyridinyl)thien-2-ylcarbonyl]-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepineYield 94.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a cooled solution (0° C.) of 0.23 g of 5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine, 523 μl of N,N-diisopropylethylamine in 5 ml of dichloromethane is added 0.436 g of 5-(2-pyridinyl)thiophene-2-carbonyl chloride. The mixture is stirred at room temperature for 16 hours under argon and diluted with 40 ml of CH2Cl2 and 20 ml of water. The organic layer is separated and washed with 20 ml each of 1N NaHCO3, brine and dried (Na2SO4). The solution is filtered through a thin pad of hydrous magnesium silicate and the filtrate concentrated to dryness. The residue is crystallized from ethyl acetate plus a small amount of hexane to give 0.485 g of tan crystals, m.p. 150°-154° C.

Workup

  1. customThe organic layer is separated
  2. washwashed with 20 ml each of 1N NaHCO3, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationThe solution is filtered through a thin pad of hydrous magnesium silicate
  5. concentrationthe filtrate concentrated to dryness
  6. customThe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-a5027326d6de40feb5ae0fdfaccdd9c5
Source dataset
uspto-grants-1997_08
Patent number
US05654297

Reaction notes

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