1,4-Dioxa-8-azaspiro(4.5)decane → 1-Naphthalenecarbonitrile, 4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-

HRID 916319Notes

Reaction equation

HRID 916319 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:11]([C:13]1(F)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH2:14]1)#[N:12]>C1COCC1>[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([C:16]3[C:17]4[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:13]([C:11]#[N:12])=[CH:14][CH:15]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 69224741HCID 69224741, compound

Product 1

HCID 115874191-Naphthalenecarbonitrile, 4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-Yield 61.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.4-dioxa-8-azaspiro[4.5]decane (332 mg, 2.32 mmol) was added to a solution of 1-cyano-1-fluoronaphthalene (120 mg, 0.70 mmol) in anhydrous THF (1 mL). After 48 hours stirring at rt the mixture was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered and evaporated to dryness. The residue was washed with a mixture of ethyl acetate and n-heptane (50:50). Purification by silica gel column chromatography, eluting with 5% methanol in dichloromethane afforded the desired compound (126 mg, 43%). The compound was converted to the corresponding hydrochloride salt as described above.

Workup

  1. customwas partitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. washThe residue was washed with a mixture of ethyl acetate and n-heptane (50:50)
  6. customPurification by silica gel column chromatography
  7. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-250a8006fea54a719e628046b23ed6a6
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

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