Diisopropylethylamine → HCID 69605138, compound
Reaction equation
BrC1C=CC(S(O[CH2:12][C@@H:13]2[O:27][C:17]3=[C:18]4[C:23](=[CH:24][CH:25]=[C:16]3[O:15][CH2:14]2)[N:22]=[C:21]([CH3:26])[CH:20]=[CH:19]4)(=O)=O)=CC=1.Cl.Cl.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)=[CH:33][CH:32]=1.C(N(CC)C(C)C)(C)C>CS(C)=O.C(=O)(O)[O-].[Na+]>[Cl:30][C:31]1[CH:32]=[CH:33][C:34]([N:37]2[CH2:42][CH2:41][N:40]([CH2:12][C@@H:13]3[O:27][C:17]4=[C:18]5[C:23](=[CH:24][CH:25]=[C:16]4[O:15][CH2:14]3)[N:22]=[C:21]([CH3:26])[CH:20]=[CH:19]5)[CH2:39][CH2:38]2)=[CH:35][CH:36]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 75 °C
Procedure
To a mixture of [(2R)-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinolin-2-yl]methyl 4-bromobenzenesulfonate (577 mg, 1.28 mmol) and 4-chlorophenylpiperazine dihydrochloride (1.03 g, 3.81 mmol) in anhydrous DMSO (10 mL) was added N,N-diisopropylethylamine (1.33 mL, 3.81 mmol). The reaction mixture was heated at 75° C. overnight. The cooled reaction mixture was diluted with saturated aqueous sodium bicarbonate solution (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. Flash chromatography on silica gel (50% hexanes/EtOAc) afforded 260 mg (15%) of the title compound as a tan solid: MS EI m/z 410.09 [M+H]+.
Workup
- customThe cooled reaction mixture
- extractionextracted with ethyl acetate (3×50 mL)
- dry with materialThe combined organic layers were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-ac4f0e8a17414dffb05e9602e9968486
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07153849B2
Reaction notes
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