Benzaldehyde → (+/-)-7-Phenyl-1,3-dioxa-8-azaspiro[4.5]decane

HRID 1872761Notes

Reaction equation

HRID 1872761 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(CC[NH2:17])OCCO1.[CH3:18][C:19]1[CH:24]=[CH:23]C(S(O)(=O)=O)=C[CH:20]=1.[C:29]([O-:32])([O-])=[O:30].[K+].[K+]>C1(C)C=CC=CC=1>[C:2]1([CH:1]2[NH:17][CH2:23][CH2:24][C:19]3([O:32][CH2:29][O:30][CH2:20]3)[CH2:18]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 6101p-Toluenesulfonic acidHCID 11430Potassium CarbonateHCID 109424562-(2-Methyl-1,3-dioxolan-2-yl)ethanamine

Product 1

HCID 18687511(+/-)-7-Phenyl-1,3-dioxa-8-azaspiro[4.5]decaneYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of benzaldehyde (10.6 g) and 2-methyl-1,3-dioxolane-2-ethanamine (13.1 g) in toluene (100 ml) was stirred for 16 hours at RT. This solution was added at 100° C. to a solution of 4-methylbenzenesulfonic acid (34.4 g) in toluene (100 ml) and the mixture was stirred for 1 hour at 100° C. The mixture was poured into an ice/water bath, K2CO3 was added to a pH of about 8 and extracted with ethyl acetate. The organic layer was dried, filtered and the solvent evaporated, yielding 14.3 g (70%) of (±)-7-phenyl-1,3-dioxa-8-azaspiro[4.5]decane (interm. 11).

Workup

  1. additionThe mixture was poured into an ice/water bath
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-6b5e88b525ab49b39f5cd4b6c6764c6c
Source dataset
uspto-grants-2000_08
Patent number
US06110939

Reaction notes

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