Piperidine → 5-morpholino-3-(piperidin-1-yl)-7H-thieno[3,2-b]pyran-7-one

HRID 1042034Notes

Reaction equation

HRID 1042034 reaction equation
Br[C:2]1[C:6]2[O:7][C:8]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[CH:9][C:10](=[O:11])[C:5]=2[S:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O=C1CCCCC1C(OCC)=O.[NH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>[Cu]I>[O:15]1[CH2:16][CH2:17][N:12]([C:8]2[O:7][C:6]3[C:2]([N:36]4[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]4)=[CH:3][S:4][C:5]=3[C:10](=[O:11])[CH:9]=2)[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 10796Cesium carbonateHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 441811783-Bromo-5-(morpholin-4-yl)-7H-thieno[3,2-b]pyran-7-one

Product 1

HCID 441808565-morpholino-3-(piperidin-1-yl)-7H-thieno[3,2-b]pyran-7-one

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
150 °C

Procedure

A 0.5 mL microwave vial was charged with a magnetic stirring bar, 3-bromo-5-morpholino-7H-thieno[3,2-b]pyran-7-one (103) (50 mg, 158 μmol), cesium carbonate (103 mg, 316 mop, copper (1) iodide (3 mg, 31 μmol), ethyl 2-oxocyclohexanecarboxylate (10 μL, 63 μmol), and piperidine (200 μL). The reaction mixture was sealed, and the reaction mixture was magnetically stirred and heated via microwave irradiation to 150° C. for 15 minutes to give 5-morpholino-3-(piperidin-1-yl)-7H-thieno[3,2-b]pyran-7-one (71).

Workup

  1. additionA 0.5 mL microwave vial was charged with a magnetic stirring bar
  2. customThe reaction mixture was sealed

Sources & evidence

ORD record
ord-47073b3f8a5d433cb2dbfbdce3c2d8a2
Source dataset
uspto-grants-2013_10
Patent number
US08557807B2

Reaction notes

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