Water → HCID 19760357, compound

HRID 1586973Notes

Reaction equation

HRID 1586973 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:18][C:19]1[CH:31]=[CH:30][C:22]([C:23]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=1.O>C(#N)C>[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([CH2:18][C:19]3[CH:31]=[CH:30][C:22]([C:23]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 22632112HCID 22632112, compound

Product 1

HCID 19760357HCID 19760357, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

1,4-Dioxa-8-azaspiro[4.5]-decane (200 mmol, 28.6 g, 25.6 mL) is dissolved in 160 ml of dry acetonitrile under nitrogen and treated with K2CO3 (220 mmol, 30.3 g) followed by dropwise addition over 1.5 hours of 4-(bromomethyl)-N,N-diethylbenzamide (200 mmol, 54.01 g) as a solution in 81 mL of acetonitrile. After 16 hours, the reaction mixture is poured into 250 mL of water and extracted twice with 150 mL of methylene chloride. The pooled extracts were washed with 250 mL of brine, dried over Na2SO4 and concentrated in vacuo affording 63.9 g (192 mmol, 96% yield) of the product as a yellow-orange oil.

Workup

  1. extractionextracted twice with 150 mL of methylene chloride
  2. washThe pooled extracts were washed with 250 mL of brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b2a5b12ed5b9467d885e1ebf95341e49
Source dataset
uspto-grants-1993_06
Patent number
US05216165

Reaction notes

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