Water → HCID 57513872, compound

HRID 2262725Notes

Reaction equation

HRID 2262725 reaction equation
[CH2:1]([N:8]1[C:16]2([CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:24][C:25]([N:27]1[CH2:32][CH2:31][N:30]([CH:33]2[CH2:36][CH2:35][CH2:34]2)[CH2:29][CH2:28]1)=[O:26].C([O-])([O-])=O.[K+].[K+].O>CC#N.CCOC(C)=O>[CH2:1]([N:8]1[C:16]2([CH2:21][CH2:20][N:19]([CH2:24][C:25]([N:27]3[CH2:32][CH2:31][N:30]([CH:33]4[CH2:36][CH2:35][CH2:34]4)[CH2:29][CH2:28]3)=[O:26])[CH2:18][CH2:17]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 574205621-(Chloroacetyl)-4-cyclobutylpiperazineHCID 57513871HCID 57513871, compound

Product 1

HCID 57513872HCID 57513872, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-benzylspiro[isoindole-1,4′-piperidin]-3(2H)-one (1.84 mmol) and 1-(chloroacetyl)-4-cyclobutylpiperazine (1.84 mmol) in CH3CN (8 ml) is added K2CO3 (761 mg, 5.52 mmol). The resulting suspension is stirred at rt overnight. Water (10 ml) and EtOAc (10 ml) is added and the layers are separated. The aqueous layer is extracted with EtOAc (20 ml) and the combined extracts are washed with brine (20 ml), dried over Na2SO4 and evaporated. The residue is purified by flash column to give 2-benzyl-1′-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]spiro[isoindole-1,4′-piperidin]-3(2H)-one as an off-white solid (LC-MS (M+1): 472.3) and 2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl 2-benzyl-3-oxo-2,3-dihydro-1′H-spiro[isoindole-1,4′-piperidine]-1′-carboxylate as a minor product.

Workup

  1. customthe layers are separated
  2. extractionThe aqueous layer is extracted with EtOAc (20 ml)
  3. washthe combined extracts are washed with brine (20 ml)
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue is purified by flash column

Sources & evidence

ORD record
ord-5c5411020db6457c9ad87c415105bb40
Source dataset
uspto-grants-2010_12
Patent number
US07851474B2

Reaction notes

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