1,1'-Carbonyldiimidazole → 8-(Phenylmethyl)-3-oxa-1,8-diazaspiro[4.5]decan-2-one

HRID 1011217Notes

Reaction equation

HRID 1011217 reaction equation
[NH2:1][C:2]1([CH2:15][OH:16])[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[C:17](N1C=CN=C1)(N1C=CN=C1)=[O:18]>ClCCl>[CH2:8]([N:5]1[CH2:6][CH2:7][C:2]2([CH2:15][O:16][C:17](=[O:18])[NH:1]2)[CH2:3][CH2:4]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 22020939HCID 22020939, compound

Product 1

HCID 577809438-(Phenylmethyl)-3-oxa-1,8-diazaspiro[4.5]decan-2-oneYield 89.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.04 g (4.72 mmol) of 4-amino-1-benzyl-4-hydroxymethylpiperidine (for preparation see: Eur. J. Med. Chim. Ther. (1974) 9, 424-433) are suspended in 16 ml of dichloromethane and 842 mg (5.2 mmol) of carbonyldiimidazole are added. As the reaction progresses, a solution forms, which following complete reaction is diluted with dichloromethane and washed first with water, then with a 5 percent sodium bicarbonate solution and once again with water. The organic phase is dried over sodium sulfate and freed from the solvent on a rotary evaporator. 1.04 g of the title compound are obtained as a crude product, which is reacted further as it is.

Workup

  1. customAs the reaction progresses
  2. customreaction
  3. washwashed first with water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customfreed from the solvent on a rotary evaporator

Sources & evidence

ORD record
ord-c1b0e9b96527427d98eff50395001bf4
Source dataset
uspto-grants-2011_07
Patent number
US07977349B2

Reaction notes

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