Diisopropylethylamine → 1-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-2-[4-(4-methoxy-benzothiazole-2-carbonyl)-piperidin-1-yl]-ethanone

HRID 1012942Notes

Reaction equation

HRID 1012942 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[O:13])[S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl[CH2:21][C:22]([C:24]1[CH:33]=[CH:32][C:27]2[O:28][CH2:29][CH2:30][O:31][C:26]=2[CH:25]=1)=[O:23].CCN(C(C)C)C(C)C>CN(C=O)C>[O:28]1[C:27]2[CH:32]=[CH:33][C:24]([C:22](=[O:23])[CH2:21][N:17]3[CH2:18][CH2:19][CH:14]([C:12]([C:10]4[S:11][C:7]5[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=5[N:9]=4)=[O:13])[CH2:15][CH2:16]3)=[CH:25][C:26]=2[O:31][CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27801786-Chloroacetyl-1,4-benzodioxaneHCID 67315952(4-Methoxy-benzothiazol-2-yl)-piperidin-4-yl-methanone

Product 1

HCID 119990461-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-2-[4-(4-methoxy-benzothiazole-2-carbonyl)-piperidin-1-yl]-ethanoneYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (4-methoxy-benzothiazol-2-yl)-piperidin-4-yl-methanone (333 mg, 1.2 mmol) and 2-chloro-1-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-ethanone (256 mg, 1.2 mmol) in DMF (4 ml) was treated with DIPEA (199 ul, 1.2 mmol) and the mixture was stirred at RT overnight. The mixture was poured on water and extracted with EtOAc. The organic layers were dried over MgSO4 and concentrated. Chromatography on SiO2 (hex/EtOAc 1:1, EtOAc) and crystallisation from ether gave 350 mg (65%) of title compound as a yellowish solid.

Workup

  1. additionThe mixture was poured on water
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. customChromatography on SiO2 (hex/EtOAc 1:1, EtOAc) and crystallisation from ether

Sources & evidence

ORD record
ord-ce9fd1e87cf74b9a8199bec2d517053f
Source dataset
uspto-grants-2011_07
Patent number
US07981886B2

Reaction notes

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