3H-spiro(isobenzofuran-1,4'-piperidin)-3-one → 1'-(1,4-Dioxa-spiro[4.5]dec-8-yl-carbamoyl)-spiro[isobenzofuran-1,4'piperidin]-3-one

HRID 413262Notes

Reaction equation

HRID 413262 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[O:15])[O:7]2)[CH2:3][CH2:2]1.[O:16]1[C:20]2([CH2:25][CH2:24][CH:23]([NH:26][C:27](Cl)=[O:28])[CH2:22][CH2:21]2)[O:19][CH2:18][CH2:17]1>CCOC(C)=O>[O:16]1[C:20]2([CH2:25][CH2:24][CH:23]([NH:26][C:27]([N:1]3[CH2:6][CH2:5][C:4]4([C:14]5[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=5)[C:8](=[O:15])[O:7]4)[CH2:3][CH2:2]3)=[O:28])[CH2:22][CH2:21]2)[O:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 98342553H-spiro(isobenzofuran-1,4'-piperidin)-3-oneHCID 22325328(1,4-Dioxa-spiro[4.5]dec-8-yl)-carbamoyl chloride

Product 1

HCID 101782031'-(1,4-Dioxa-spiro[4.5]dec-8-yl-carbamoyl)-spiro[isobenzofuran-1,4'piperidin]-3-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Add spiro[isobenzofuran-1,4′-piperidin]-3-one (100 mg, 0.49 mmol) to 1 mL of the stock solution of (1,4-dioxa-spiro[4.5]dec-8-yl)-carbamoyl chloride (˜0.2 M in toluene) and heat to 60° C. for 16 hours. Cool the solution, dilute with EtOAc and wash with brine. Dry the solution (Na2SO4) and concentrate under reduced pressure. Purify the crude product using preparative plate chromatography and triturate the resulting material with ether to obtain 1′-(1,4-dioxa-spiro[4.5]dec-8-yl-carbamoyl)-spiro[isobenzofuran-1,4′-piperidin]-3-one as a white solid.

Workup

  1. temperatureCool the solution
  2. washwash with brine
  3. dry with materialDry the solution (Na2SO4)
  4. concentrationconcentrate under reduced pressure
  5. customPurify the crude product
  6. customtriturate the resulting material with ether

Sources & evidence

ORD record
ord-cc39f187ed194b93940a4a0cde224fb9
Source dataset
uspto-grants-2003_05
Patent number
US06566367B2

Reaction notes

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