1,2,3,6-Tetrahydropyridine → 1-[(1,4-Dioxa-8-azaspiro[4.5]dec-7-yl)carbonyl]-1,2,3,6-tetrahydropyridine

HRID 1196509Notes

Reaction equation

HRID 1196509 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH:7]([C:11]([O:13]C)=O)[CH2:6]2)[O:4][CH2:3][CH2:2]1.[NH:15]1[CH2:20][CH:19]=[CH:18][CH2:17][CH2:16]1>>[O:4]1[C:5]2([CH2:10][CH2:9][NH:8][CH:7]([C:11]([N:15]3[CH2:16][CH:17]=[CH:18][CH2:19][CH2:20]3)=[O:13])[CH2:6]2)[O:1][CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 127501,2,3,6-TetrahydropyridineHCID 15123245Methyl 1,4-dioxa-8-azaspiro[4.5]decane-7-carboxylate

Product 1

HCID 198988591-[(1,4-Dioxa-8-azaspiro[4.5]dec-7-yl)carbonyl]-1,2,3,6-tetrahydropyridine

Conditions

Temperature
150 °C

Procedure

A mixture of the product of Example 1 stage (iv) (1 g) and 1,2,3,6-tetrahydropyridine (2.8 ml) was heated at 150° C. in a reactivial for 2 h. After cooling the mixture was evaporated in vacuo and the solid residue (800 mg) was purified by flash chromatography eluting with dichloromethane/methanol/ammonia (200:10:1) to give the title compound as an oil (260 mg). T.l.c. Silica, dichloromethane/methanol/ammonia (150:8:1) Rf 0.25.

Workup

  1. temperatureAfter cooling the mixture
  2. customwas evaporated in vacuo
  3. customthe solid residue (800 mg) was purified by flash chromatography
  4. washeluting with dichloromethane/methanol/ammonia (200:10:1)

Sources & evidence

ORD record
ord-574f7f11070d4a91974abff77d1fc03c
Source dataset
uspto-grants-1992_05
Patent number
US05114945

Reaction notes

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