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

HRID 1182735
Notes
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Reaction equation

HRID 1182735 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 98342553H-spiro(isobenzofuran-1,4'-piperidin)-3-oneHCID 68629339HCID 68629339, compound

Product 1

HCID 46213795HCID 46213795, compoundYield 14.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 31347SulfolaneSolvent

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

  1. additionThe reaction mixture was poured on water
  2. extractionextracted with tert-butyl methyl ether
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes