3H-spiro(isobenzofuran-1,4'-piperidin)-3-one → HCID 46213795, compound

HRID 1182735Notes

Reaction equation

Br[C:2]1[N:11]2[C:5]([CH2:6][N:7]([CH3:17])[CH2:8][C:9]3[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:10]=32)=[N:4][N:3]=1.[NH:18]1[CH2:23][CH2:22][C:21]2([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[C:25](=[O:32])[O:24]2)[CH2:20][CH2:19]1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.S1(CCCC1)(=O)=O>[Cl:16][C:14]1[CH:13]=[CH:12][C:10]2[N:11]3[C:2]([N:18]4[CH2:23][CH2:22][C:21]5([C:27]6[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=6[C:25](=[O:32])[O:24]5)[CH2:20][CH2:19]4)=[N:3][N:4]=[C:5]3[CH2:6][N:7]([CH3:17])[CH2:8][C:9]=2[CH:15]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 1-bromo-8-chloro-5-methyl-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzoazulene (50 mg, 0.16 mmol), tetrabutylammonium bromide (10 mg, 0.031 mmol) and 3H-spiro[2-benzofuran-1,4′-piperidin]-3-one (65 mg, 0.32 mmol) in sulfolane (0.5 ml) was stirred for 20 h at 160° C. The reaction mixture was poured on water and extracted with tert-butyl methyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo. Residual sulfolane was evaporated by kugelrohrdistillation (120° C., 1-2 mbar). Preparative HPLC with n-heptane/2-propanol (70:30) as eluent gave the title compound (10 mg, 14%) as light yellow solid. MS m/e: 436 (M+H+).

Workup

additionThe reaction mixture was poured on water
extractionextracted with tert-butyl methyl ether
washThe organic layer was washed with water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customResidual sulfolane was evaporated by kugelrohrdistillation (120° C., 1-2 mbar)

Sources & evidence

ORD record: ord-e5b1570fe7a04413a4073bd9d7db841f
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664216B2

Reaction notes

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